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

HRID 491631

Reaction equation

HRID 491631 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d9c24b3c6a0d486cb91bee5fb968016a
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Linked notes

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