Sodium Hydroxide → 4-(Aminomethyl)-2-chloroaniline

HRID 14404

반응식

HRID 14404 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[Cl:16].[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][C:9]=1[Cl:16]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 5198964-Amino-3-chlorobenzonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 218806504-(Aminomethyl)-2-chloroaniline수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To lithium aluminum hydride (2.11 g, 55.6 mmol) in dry THF (50 mL) was added dropwise 4-amino-3-chlorobenzonitrile (3.29 g, 21.6 mmol) in THF (40 mL). The mixture was stirred at RT for 16 hours. Then, 6.0 mL of 1.0 N NaOH solution was added dropwise and the reaction mixture was stirred for 20 min. The solid was filtered off and washed with THF for three times. The solvent was removed by rotavap to give 4-amino-3-chlorobenzylamine as an oily liquid (3.04 g, 90%). 1H NMR (500 MHz, CD3OD): δ 7.18 (d, J=2Hz, 1H), 7.00 (dd, J=8Hz, 2Hz, 1H), 6.78 (d, J=8Hz, 1H), 3.61 (s, 2H).

후처리

  1. stirringthe reaction mixture was stirred for 20 min
  2. filtrationThe solid was filtered off
  3. washwashed with THF for three times
  4. customThe solvent was removed by rotavap

출처 및 근거

ORD 기록
ord-165a5394ee0844deb8f9d0413dd1b106
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732434B2

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