HCID 15230626, compound → HCID 15342417, compound

HRID 259860Notes

Reaction equation

HRID 259860 reaction equation
C([O:4][C:5]1[C:6]([CH3:39])=[C:7]([CH3:38])[C:8]2[O:12][C:11]([CH3:35])([C:13]([NH:15][C:16]3[CH:17]=[N:18][C:19]4[C:24]([C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:23][C:22]([CH3:33])=[CH:21][C:20]=4[CH3:34])=[O:14])[CH2:10][C:9]=2[C:36]=1[CH3:37])(=O)C.Cl.CO>O>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]1[C:24]2[C:19](=[C:20]([CH3:34])[CH:21]=[C:22]([CH3:33])[CH:23]=2)[N:18]=[CH:17][C:16]=1[NH:15][C:13]([C:11]1([CH3:35])[CH2:10][C:9]2[C:36]([CH3:37])=[C:5]([OH:4])[C:6]([CH3:39])=[C:7]([CH3:38])[C:8]=2[O:12]1)=[O:14]

Participants

4

Reactant 2

HCID 15230626HCID 15230626, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 15342417HCID 15342417, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(5-acetoxy-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-ylcarbonyl)amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (400 mg) and 6.92N-hydrochloric acid-methanol solution (10 ml) was stirred at room temperature for eight hours. After addition of water, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then concentrated. The residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1,V/V), and then crystallized from isopropyl ether to give 4-(2-chlorophenyl)-3-(2,3-dihydro-5-hydroxy-2,4,6,7-tetramethylbenzofuran-2-ylcarbonyl)amino-6,8-dimethylquinoline (104 mg, 28.2%) as colorless prisms.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1,V/V)
  6. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-50d5d324e42a4cb48e3ad34865d73ab4
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Reaction notes

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