5-(Benzyloxy)-4-methoxy-2-nitrobenzamide → 2-Amino-5-(benzyloxy)-4-methoxybenzamide

HRID 61643ノート

反応式

HRID 61643 の反応式
[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:20]([O-])=O)[CH:4]=1>C(O)(=O)C.CO.[Fe]>[CH3:1][O:2][C:3]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH2:20])[CH:4]=1

参加物

4

反応物 1

HCID 593618645-(Benzyloxy)-4-methoxy-2-nitrobenzamide

生成物 1

HCID 593619042-Amino-5-(benzyloxy)-4-methoxybenzamide収率 87.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 10129899Acetic acid methanol溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4-methoxy-5-benzyloxy-2-nitrobenzamide (6.60 g, 21.9 mmol) and iron powder (8.14 g, 0.146 mol) in acetic acid/methanol (80 mL/80 mL) was heated at 85±5° C. for 1.5 h. The reaction mixture was allowed to cool to RT and the iron was removed by filtration, and volatiles were removed in vacuo. The residue was taken up in sat. sodium bicarbonate and the mixture was extracted with ethyl acetate (600 mL×3). The combined organic layers were washed with water (1×150 mL), brine (1×150 mL), dried (Na2SO4), filtered and concentrated in vacuo to give 4-methoxy-5-benzyloxy-2-aminobenzamide (5.2 g, 19.1 mmol, 87%). MS 273.2. (M+). HPLC retention time 4.585 min.

後処理

  1. temperatureto cool to RT
  2. customthe iron was removed by filtration, and volatiles
  3. customwere removed in vacuo
  4. extractionthe mixture was extracted with ethyl acetate (600 mL×3)
  5. washThe combined organic layers were washed with water (1×150 mL), brine (1×150 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-57fdcff184644828abcbbea73c529a91
出典データセット
uspto-grants-2016_09
特許番号
US09440961B2

反応ノート

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