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

HRID 491631

반응식

HRID 491631 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9c24b3c6a0d486cb91bee5fb968016a
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531553B2

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