Methanol → N-(5-amino-2-tert-butyl-phenyl)-formamide

HRID 74031

반응식

HRID 74031 반응식
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[C:13]([NH:21][CH:22]=[O:23])[CH:12]=1)C1C=CC=CC=1.CO>[Pd].C(Cl)Cl>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[C:13]([NH:21][CH:22]=[O:23])[CH:12]=1

참가 물질

5

반응물 2

HCID 887MethanolHCID 57896237(4-Tert-butyl-3-formylamino-phenyl)-carbamic acid benzyl ester

생성물 1

HCID 57896236N-(5-amino-2-tert-butyl-phenyl)-formamide수율 96%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6344Dichloromethane용매

실험 절차

A 100 mL flask was charged with (4-tert-butyl-3-formylamino-phenyl)-carbamic acid benzyl ester (650 mg, 1.99 mmol), methanol (30 mL) and 10% Pd—C (50 mg), and stirred under H2 (1 atm) for 20 h. CH2Cl2 (5 mL) was added to quench the catalyst, and the mixture then filtered through Celite, and concentrated to afford N-(5-amino-2-tert-butyl-phenyl)-formamide as an off-white solid (366 mg, 96%). Rotameric by 1H and 13C NMR (DMSO-d6). 1H NMR (400 MHz, DMSO-d6, rotameric) δ 9.24 (d, J=10.4 Hz, 1H), 9.15 (s, 1H), 8.23 (d, J=1.5 Hz, 1H), 8.06 (d, J=10.4 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 7.02 (d, J=8.5 Hz, 1H), 6.51 (d, J=2.5 Hz, 1H), 6.46 (dd, J=2.5, 8.5 Hz, 1H), 6.39 (dd, J=2.5, 8.5 Hz, 1H), 6.29 (d, J=2.5 Hz, 1H), 5.05 (s, 2H), 4.93 (s, 2H), 1.27 (s, 9H); 13C NMR (100 MHz, DMSO-d6, rotameric) δ 164.0, 160.4, 147.37, 146.74, 135.38, 135.72, 132.48, 131.59, 127.31, 126.69, 115.15, 115.01, 112.43, 112.00, 33.92, 33.57, 31.33, 30.92; ESI-MS 193.1 m/z (MH+).

후처리

  1. customto quench the catalyst
  2. filtrationthe mixture then filtered through Celite
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-89363dce21f64286a71ced2e136a59fe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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