2,4-Dichloroaniline → Anthranilamide

HRID 1987505Notes

Reaction equation

HRID 1987505 reaction equation
ClC1C=C(Cl)C=CC=1[NH2:4].[H-].[Na+].[N+:12]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18])([O-])=O>CN(C=O)C>[NH2:12][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH2:4])=[O:18]

Participants

5

Reactant 3

HCID 111232,4-DichloroanilineHCID 118752-Nitrobenzoyl chlorideHCID 24758Sodium hydride

Product 1

HCID 6942Anthranilamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-dichloro-aniline (322 mg, 2.0 mmol) in DMF was treated with 95% NaH (53 mg, 2.1 mmol) at 0° C., and then 2-nitro-benzoyl chloride was added (390 mg, 2.1 mmol). After stirring for 2 h at rt, the mixture was concentrated and co-evaporated with water, diluted with CH2Cl2, washed with aq. NaHCO3, dried and concentrated. The crude residue was dissolved in EtOH, and subjected to hydrogenation at 1 atm overnight, filtered through Celite and concentrated to give the crude product 2-amino-benzamide.

Workup

  1. concentrationthe mixture was concentrated and co-evaporated with water
  2. additiondiluted with CH2Cl2
  3. washwashed with aq. NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe crude residue was dissolved in EtOH
  7. customsubjected to hydrogenation at 1 atm overnight
  8. filtrationfiltered through Celite
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4e5c3a75888747e992392c92feb1cecb
Source dataset
uspto-grants-2009_06
Patent number
US07550590B2

Reaction notes

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