Sodium Hydroxide → HCID 21851157, compound

HRID 1458917Notes

Reaction equation

HRID 1458917 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-dimethoxyphenyl)-2-[(1-methylimidazol-2-yl)thiomethyl]-quinoline-3-carboxylate (0.6 g), 2N sodium hydroxide (1.7 ml) and ethanol (12 ml) was refluxed for 6 hours. The reaction mixture was concentrated in vacuo. The residue was diluted with water, washed with ethyl acetate, made acidic with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated in vacua to give crystals. The crystals were recrystallized from ethanol-ethyl ether to give 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 water
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacua
  9. customto give crystals
  10. customThe crystals were recrystallized from ethanol-ethyl ether

Sources & evidence

ORD record
ord-7f633abef242411caf5c59a27eeb0ad7
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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