4-Chloro-2-nitroaniline → 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

HRID 491631

反応式

HRID 491631 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1>CN(C=O)C>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([NH:7][CH3:8])=[O:6])=[CH:16][C:17]=1[N+:22]([O-:24])=[O:23]

参加物

5

反応物 3

HCID 69794-Chloro-2-nitroanilineHCID 24758Sodium hydrideHCID 3537103-hydroxy-N-methylbenzamide

生成物 1

HCID 690175323-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-hydroxy-N-methyl-benzamide (Step A, 700 mg, 4.6 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added NaH (200 mg, 5.1 mmol, 1.1 eq.). The reaction was stirred for 10 min. at RT after which 4-chloro-2-nitro-phenylamine (2.0 g, 11.6 mmol, 2.5 eq.) was added. The resulting mixture was heated to 80° C. for 4 h. The reaction was quenched with NaHCO3 (aq.), diluted with CH2Cl2 (50 mL), and washed with 1 N NaOH (25 mL). The organic layer was dried over MgSO4, filtered and concentrated. The crude was further purified by column chromatography (0-100% EtOAc in hexanes) to give pure 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide.

後処理

  1. additionwas added
  2. customThe reaction was quenched with NaHCO3 (aq.)
  3. additiondiluted with CH2Cl2 (50 mL)
  4. washwashed with 1 N NaOH (25 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was further purified by column chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-d9c24b3c6a0d486cb91bee5fb968016a
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

関連ノート

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