Pyridine → HCID 67770498, compound

HRID 259865Notes

Reaction equation

HRID 259865 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 67770498HCID 67770498, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-dimethoxycinnamoyl chloride (678 mg), 3-amino-4-(2-chlorophenyl)-1,6,8-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-e83d4e6373dc467487da94c93fa7144d
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Reaction notes

Loading…