Triethylamine → 8-Amino-4-quinolinyl 2,6-dichlorobenzoate

HRID 613477Notes

Reaction equation

HRID 613477 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[OH:12].[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=1[C:16](Cl)=[O:17].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>CC(N(C)C)=O.O>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C:16](=[O:17])[C:15]1[C:14]([Cl:13])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 783922,6-Dichlorobenzoyl chlorideHCID 178507422HCID 178507422, compound

Product 1

HCID 195924468-Amino-4-quinolinyl 2,6-dichlorobenzoateYield 38.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 8-amino-4-hydroxyquinoline (300 mg), 2,6-dichlorobenzoyl chloride (432 mg), triethylamine (569 mg) and catalytic amount of dimethylaminopyridine in dimethylacetamide (3 ml) was stirred for 1 hour under ice-cooling. To the mixture was added water (3 ml) and the resulting precipitate was collected by filtration. The residue was suspended in hot ethanol (10 ml) with stirring. The resulting precipitate was collected by filtration, and the residue was purified by flash chromatography (ethyl acetate-dichloromethane) to give 8-amino-4-(2,6-dichlorobenzoyloxy)quinoline (240 mg).

Workup

  1. temperaturecooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. stirringwith stirring
  4. filtrationThe resulting precipitate was collected by filtration
  5. customthe residue was purified by flash chromatography (ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-1383859075d944eeb21e09d864153704
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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