Sodium Hydroxide → HCID 21851157, compound

HRID 617227Notes

Reaction equation

HRID 617227 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH2:15][S:16][C:17]1[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=1)[C:7]([C:23]([O:25]CC)=[O:24])=[C:6]2[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH2:15][S:16][C:17]1[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=1)[C:7]([C:23]([OH:25])=[O:24])=[C:6]2[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10768373HCID 10768373, compound

Product 1

HCID 21851157HCID 21851157, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6,7-dimethoxy-4-(3,4-dimethoxy- phenyl)-2-[(1-methylimidazol-2-yl)thiomethyl]quinoline-3-carboxylate (0.6 g), 2N NaOH (1.7 ml) and ethanol (12 ml) was refluxed for 6 hours. The reaction mixture was concentrated in vacuo. The residue was diluted with H2O, washed with ethyl acetate, acidified with 2N HCl and extracted with ethyl acetate. The extract was washed with H2O, dried over MgSO4, and concentrated in vacuo to give crystals. Recrystallization from ethanol-ethyl ether gave 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[(1-methylimidazol-2-yl)thiomethyl]quinoline-3-carboxylic acid (0.3 g, 53%) as colorless prisms, mp 213-214° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted with H2O
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with H2O
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give crystals
  10. customRecrystallization from ethanol-ethyl ether

Sources & evidence

ORD record
ord-6135d5c7a91e4a4a96e10c69d4bcb8f1
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

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