Pyridine → 4-(2-chlorophenyl)-3-(3,4-dimethoxycinnamoylamino)-1,6,8-trimethyl-2(1H)-quinolone hydrate

HRID 2379490Notes

Reaction equation

HRID 2379490 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](Cl)=[O:9].[NH2:16][C:17]1[C:18](=[O:37])[N:19]([CH3:36])[C:20]2[C:25]([C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:33])=[CH:24][C:23]([CH3:34])=[CH:22][C:21]=2[CH3:35].N1C=CC=CC=1.C1COCC1>O>[OH2:2].[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26]1[C:25]2[C:20](=[C:21]([CH3:35])[CH:22]=[C:23]([CH3:34])[CH:24]=2)[N:19]([CH3:36])[C:18](=[O:37])[C:17]=1[NH:16][C:8](=[O:9])[CH:7]=[CH:6][C:5]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 224039003-amino-4-(2-chlorophenyl)-l,6,8-trimethyl-2(1H)quinoloneHCID 533992063,4-Dimethoxycinnamoylchloride

Product 1

HCID 677704984-(2-chlorophenyl)-3-(3,4-dimethoxycinnamoylamino)-1,6,8-trimethyl-2(1H)-quinolone hydrateYield 65.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-dimethoxycinnamoyl chloride (678 mg), 3-amino-4-(2-chlorophenyl)-l,6,8-trimethyl-2(1H)quinolone (511 mg), pyridine (0.28 ml) and THF (10 ml) was stirred at room temperature for four days. Then, the mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed and the residue was purified by a silica gel chromatography with benzene-acetone (4:1) to give crystals of 4-(2-chlorophenyl)-3-(3,4-dimethoxycinnamoylamino)-1,6,8-trimethyl-2(1H)-quinolone hydrate (510 mg, 65.6%). The crystals were recrystallized from ethanol to afford colorless prisms.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed
  5. customthe residue was purified by a silica gel chromatography with benzene-acetone (4:1)

Sources & evidence

ORD record
ord-2090fd21fc084f17951427dd1f0d3b46
Source dataset
uspto-grants-1994_11
Patent number
US05362742

Reaction notes

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