20.5 Preparation of Amines

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1 RGANIC CHEMISTRY 20.5 Preparation of Amines

2 RGANIC CHEMISTRY 20.5A Through Nucleophilic Substitution Reactions Alkylation of Ammonia or Amines NaH NH 3 + R X RNH 3 X RNH2 R + R X R 2 X NaH R 2 NH R 2 NH + R X R 3 NH X R 3 N R 3 N + R X R 4 N X NaH This method is of very limited synthetic application because multiple alkylations occur.

3 RGANIC CHEMISTRY Alkylation of Azide Ion and Reduction R X + N N N (NaN 3 ) Azide ion S N 2 R N N N Alkyl azide Na / alcohol or LiAlH 4 R

4 RGANIC CHEMISTRY The Gabriel Synthesis NH KH EtH N K R X N R H + or H H 2 R + C 2 H C 2 H H 2 N EtH R + NH NH

5 RGANIC CHEMISTRY 20.5B Preparation of Aromatic Amines through Reduction of Nitro Compounds Ar H HN 3 H 2 S 4 Ar N 2 [H] [H] Ar M / H + : Zn / HCl, Fe / HCl, Sn / HCl, H 2 / Catalyst (CH 3 ) 3 C N 2 H 2, Pt EtH (CH 3 ) 3 C CH 3 N 2 2 N (1) Fe, HCl (2) H CH 3 H 2 N

6 RGANIC CHEMISTRY CH 3 N 2 H2 S, NH 3 CH 3 N 2 N 2 N 2 NaSH N 2 EtH, N 2 79 ~ 85% N 2 H 2 S, NH 4 H N 2 EtH, 50 C 52 ~ 58% N 2

7 RGANIC CHEMISTRY 20.5C Preparation of Primary, Secondary, or Tertiary Amines through Reductive Amination R' R C NH 3 [H] R" [H] R"R"'NH [H] R' R CH R R R' CH R' CH NHR" NR"R"' 1 Amine 2 Amine 3 Amine

8 RGANIC CHEMISTRY C 6 H 5 CH + NH 3 (excess) H 2 / Ni EtH C 6 H 5 CH 2 R' R C + NH 3 (excess) H 2 / Ni EtH R' R CH + NH 3 (excess) H 2 / Ni EtH Reductive Amination of Ketones and Aldehydes

9 RGANIC CHEMISTRY Mechanism R' R C + NH 3 R' R C NH 3 R' R C H ( H 2 ) R' R C NH R' R C H or R' R C NH [H] R' R CH [H] : H 2 / catalyst (Ni, Pt... ); NaBH 3 CN; LiBH 3 CN

10 RGANIC CHEMISTRY Leukart Reaction Reductive amination of aldehydes or ketones by ammonium (or amine) salts of formic acid : HC 2 NH 4 RCH RCH 2

11 RGANIC CHEMISTRY Eschweiler-Clarke Reaction The reductive methylation of primary or secondary amines employing formaldehyde and formic acid: R + CH 2 HC 2 H(excess) RN(CH 3 ) 2

12 RGANIC CHEMISTRY 20.5D Preparation of Primary, Secondary, or Tertiary Amines through Reduction of Nitriles, ximes, and Amides R CN R C [H] R CH 2 R C R NH [H] LiAlH 4, H 2 / Catalyst ximes are also conveniently reduced with sodium in alcohol.

13 RGANIC CHEMISTRY N H Na, EtH (50 ~ 60%) N CH 3 CCH 3 (1) LiAlH 4 (2) H 2 NH CH 3 CH 2 CH 3 CH 3 CCl / base NH Monoalkylation of amines CH 3

14 RGANIC CHEMISTRY 20.5E Preparation of Primary Amines though the Homann and Curtius Rearrangements Hofmann Rearrangement An unsubstitued amide is treated with Br 2 /NaH (NaBr) to give a primary amine that has one carbon fewer than the starting amide. R C Br 2 NaH R + C 2

15 RGANIC CHEMISTRY Mechanism R C H R C NH Br Br R C NHBr H Br H 2 R C N Br R N C Isocyanate H 2 R N C R N H C H R NH C H C 2 R

16 RGANIC CHEMISTRY Curtius Rearrangement Formation of isocyanates by thermal decomposition of acyl azides: R C Cl + NaN 3 R C N 3 R N C (CH 3 ) 2 CHCH 2 C Cl H 2 RNH C 2 2 NaN 3 (CH 3 ) 2 CHCH 2 C N 3 CHCl 3 H 2 (CH 3 ) 2 CHCH 2 N C (CH 3 ) 2 CHCH 2 C 2 (70%)

17 RGANIC CHEMISTRY Schmidt Rearrangement R C H H 2 S 4 + HN 3 R C N 3 R N C H 2 C 2 R C 2 H + HN 3 H 2 S 4 60~80%

18 RGANIC CHEMISTRY 20.6 Reactions of Amines

19 RGANIC CHEMISTRY N + H A N H + A N + RCH 2 Br N CH 2 R + Br N H + R C Cl N H C Cl R HCl N C R + E H E + E

20 RGANIC CHEMISTRY Br 2 Br Br H 2 Aniline Br 2,4,6-Tribromoaniline (100%) I 2 NaHC 3 I

21 RGANIC CHEMISTRY (CH 3 C) 2 Pyridine NHCCH 3 NHCCH 3 Br 2 Br H 2 HCl + CH 3 C 2 H Br

22 RGANIC CHEMISTRY Vilsmeier Reaction N(CH 3 ) 2 N(CH 3 ) 2 HCN(CH 3 ) 2 H 2 PCl 3 CH 3 H PPA, 200 CH (80~84%)

23 RGANIC CHEMISTRY 20.6A xidation of Amines Primary and secondary aliphatic amines are subject to oxidation, although in most instances useful products are not obtained. Tertiary amines can be oxidized cleanly to tertiary amine oxides. Aryl amines are very easily oxidized by variety of reagents. xidation is not confined to the amino group but also occurs in the ring. R 3 N H 2 2 or RC 3 H R3 N A tertiary amine oxide

24 RGANIC CHEMISTRY Mn 2 H 2 S 4, 20 Br Br CH 3 C 3 H Br N 2 Br CH 2 Cl 2

25 RGANIC CHEMISTRY 20.7 Reactions of Amines with Nitrous Acid

26 RGANIC CHEMISTRY 20.7A Reactions of Primary Aliphatic Amines with Nitrous Acid Primary aliphatic amines react with nitrous acid through a reaction called diazotizations ( ) to yield highly unstable aliphatic diazonium salts ( ). R NaN 2, HCl R N N Cl 0 ~ 5 Aliphatic diazonium salt N 2 R RH + RX + C C...

27 RGANIC CHEMISTRY 20.7B Reactions of Primary Arylamines with Nitrous Acid Primary arylamines react with nitrous acid to give arenediazonium salts. Even though arenediazonium salts are unstable, they are still far more stable than aliphatic diazonium salts. NaN 2, HCl Ar 0 ~ 5 Primary arylamine Ar N N Cl arenediazonium salt (Stable if keep below 5 C)

28 RGANIC CHEMISTRY Mechanism H N + H + H 2 N H 2 N Ar 1 Arylamine H 3 N ArNH N ArNH N H H 2 H + H 2 ArN N H ArN N H 2 ArN N Diazohydroxide N-Nitrosoamine ArN N Diazonium ion

29 RGANIC CHEMISTRY 20.7B Reactions of Secondary Arylamines with Nitrous Acid Secondary amines both aryl and alkyl react with nitrous acid to yield N-nitrosoamines (N- ). R 2 NH Ar 2 NH NaN 2, HCl 0 ~ 5 NaN 2, HCl 0 ~ 5 R 2 N N N-nitrosoamine N- Ar 2 N N

30 RGANIC CHEMISTRY 20.7C Reactions of Tertiary Arylamines with Nitrous Acid Tertiary aliphatic amines react with nitrous acid to form its salt N-nitrosoammonium compounds NaN 2, HCl R 3 N 0 ~ 5 R 3NH N 2 Tertiary aliphatic N-Nitrosoammonium amine compound H

31 RGANIC CHEMISTRY Tertiary arylamines react with nitrous acid to form C-nitroso aromatic compounds. N(CH 3 ) 2 N,N-Dimethylaniline N,N NaN 2, HCl 8 C N N(CH 3 ) 2 4-Nitroso-N,N-dimethylaniline N,N -4- (80 90%)

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