反応 #161213

反応方程式

(4-tert-butyl-3-formylamino-phenyl)-carbamic acid benzyl ester

methanol

→

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

収率 96.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他to quench the catalyst
2. 2
   ろ過the mixture then filtered through Celite
3. 3
   濃縮concentrated

実験手順

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+).

出典