Sodium Hydroxide → HCID 15035167, compound

HRID 1656427Notes

Reaction equation

HRID 1656427 reaction equation
C([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([NH:14][C:15](=[O:36])[NH:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])=[CH:24][C:23]([CH3:34])=[CH:22][C:21]=3[CH3:35])=[CH:7][C:6]=1[CH:37]([CH3:39])[CH3:38])(=O)C.[OH-].[Na+]>CO>[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]=[CH:18][C:17]=1[NH:16][C:15]([NH:14][C:8]1[CH:9]=[C:10]([CH:11]([CH3:12])[CH3:13])[C:5]([OH:4])=[C:6]([CH:37]([CH3:39])[CH3:38])[CH:7]=1)=[O:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15035164HCID 15035164, compound

Product 1

HCID 15035167HCID 15035167, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[3-(4-acetoxy-3,5-diisopropylphenyl)ureido]-4-(2-chlorophenyl)-6,8-dimethylquinoline (300 mg), methanol (20 ml) and 1N-sodium hydroxide (2 ml) was stirred for 1.5 hrs. at room temperature. After concentrated, the mixture was diluted with water, acidified with 2N-hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and then distilled to remove the solvent. The residue was recrystallized from a mixture of acetone and isopropyl ehter to give 4-(2-chlorophenyl)-3-[3-(4-hydroxy-3,5-diisopropylphenyl)ureido]-6,8-dimethylquinoline as colorless prisms. Yield 116 mg (41.9%). m.p. 194°-196° C.

Workup

  1. customat room temperature
  2. concentrationAfter concentrated
  3. additionthe mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue was recrystallized from a mixture of acetone and isopropyl ehter

Sources & evidence

ORD record
ord-b059a0cd387c4d2588682a6e5a45ab24
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

Loading…