Acetyl chloride → Allyl 5-acetamido-2-nitrobenzoate

HRID 1736377Notes

Reaction equation

HRID 1736377 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([N+:18]([O-:20])=[O:19])=[C:10]([CH:17]=1)[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12].C(N(CC)CC)C>ClCCl>[C:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([N+:18]([O-:20])=[O:19])=[C:10]([CH:17]=1)[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19432493Allyl 5-amino-2-nitrobenzoate

Product 1

HCID 19432451Allyl 5-acetamido-2-nitrobenzoateYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of acetyl chloride (3.18 g, 40.5 mM) in dichloromethane (10 ml) under an argon atmosphere was added at 0° to a solution of allyl 5-amino-2-nitrobenzoate (3.0 g, 13.5 mM) in dichloromethane (30 ml). After addition of a solution of triethylamine (1.88 ml, 13.5 mM) in dichloromethane (10 ml) the mixture was stirred at ambient temperature overnight. The solvent was evaporated and the residue purified by chromatography on silica. Elution with ethyl acetate/petroleum ether (50/50) gave allyl 5-acetamido-2-nitrobenzoate (3.36 g, 94%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography on silica
  3. washElution with ethyl acetate/petroleum ether (50/50)

Sources & evidence

ORD record
ord-c827cefe88464077ba249dab731d45a9
Source dataset
uspto-grants-1996_07
Patent number
US05541178

Reaction notes

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