Methyl 2-methoxy-3-nitrobenzoate → Methyl 3-amino-2-methoxybenzoate

HRID 590117ノート

反応式

HRID 590117 の反応式
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CO.[Ni]>[NH2:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

4

反応物 1

HCID 590805Methyl 2-methoxy-3-nitrobenzoate

生成物 1

HCID 13338715Methyl 3-amino-2-methoxybenzoate収率 96.8%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

To a solution of methyl 2-methoxy-3-nitrobenzoate (28.4 g, 134 mmol) in MeOH (150 mL) was added Raney Ni (3 g). The mixture was stirred under H2 atmosphere (50 psi/25° C.) for 3.5 h. The catalyst was filtered, and the filtrate was concentrated under the reduced pressure to dryness to give the crude product, which was purified by recrystallization in EtOAc to afford the title compound of Step C, methyl 3-amino-2-methoxybenzoate (23.5 g, 96.4% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80-6.93 (m, 3H), 5.10-5.25 (br, 2H), 3.78 (s, 3H), 3.67 (s, 3H).

後処理

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under the reduced pressure to dryness
  3. customto give the crude product, which
  4. customwas purified by recrystallization in EtOAc

出典と根拠

ORDレコード
ord-642d437a4efb429fb834df12b75e26b3
出典データセット
uspto-grants-2016_01
特許番号
US09233956B2

反応ノート

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