Benzoyl chloride, 3,4-dichloro- → HCID 22057976, compound

HRID 2302243Notes

Reaction equation

HRID 2302243 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([NH:19][C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=[O:21])[CH:18]=1>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([NH:19][C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=[O:21])[CH:18]=1)=[O:6]

Participants

4

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 22057974HCID 22057974, compound

Product 1

HCID 22057976HCID 22057976, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Using an analogous procedure to that described in Example 4, 3,4-dichlorobenzoyl chloride was reacted with N-(5-amino-2-methylphenyl)quinoline-6-carboxamide in the presence of triethylamine. The reaction mixture was stirred at ambient temperature for 16 hours and then evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound in 57% yield; Mass Spectrum: M+H+ 450.

Workup

  1. customevaporated
  2. customThe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-7b40492aa14c4a22b896132df6d6c489
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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