Amines2 - P1: PCX/SRB JWDD052-20 P2: xxx...

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P1: PCX/SRB P2: xxx Printer: Hamilton JWDD052-20 JWDD052-Solomons-v3 June 12, 2007 21:11 20 AMINES PREPARATION AND REACTIONS OF AMINES A. Preparation 1. Preparation via nucleophilic substitution reactions. NaN 3 , ethanol NH 3 RCH 2 NH 2 + (RCH 2 ) 2 NH + (RCH 2 ) 3 N (poor method) RCH 2 RCH 2 NH 2 N 3 Na/ethanol or LiAlH 4 RCH 2 Br RCH 2 N H H NH 2 NH 2 + RCH 2 NH 2 N N O O O O ΝΚ Ο Ο 2. Preparation through reduction of nitro compounds. HNO 3 NO 2 H 2 SO 4 (1) Fe, HCl H 2 , cat. or (2) OH NH 2 3. Preparation via reductive amination. Aldehyde or ketone NH 3 [H] CO R' R ' R NH 2 R CH R " NH 2 [H] R ' R ' R NHR " R CH R " R '" NH [H] R ' R ' RN R " R '" R CH 430
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P1: PCX/SRB P2: xxx Printer: Hamilton JWDD052-20 JWDD052-Solomons-v3 June 12, 2007 21:11 AMINES 431 4. Preparation of amines through reduction of amides, oximes, and nitriles. CN H 2 Ni RCH 2 Br RCH 2 CN RCH 2 CH 2 NH 2 NH 2 OH Na/ethanol CO R ' R C R R ' CHNH 2 NOH R ' R (1) LiAlH 4 (2) H 2 O RNHR ' + R " CCl CNRR ' R " R " CH 2 NRR ' O O R (1) LiAlH 4 (2) H 2 O R ' CCl NH 2 NHCR ' R RNHCH 2 R ' O O + 5. Preparation through the Hofmann rearrangement of amides.
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Amines2 - P1: PCX/SRB JWDD052-20 P2: xxx...

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