Potassium Hydroxide → HCID 9975044, compound

HRID 1534365Notes

Reaction equation

HRID 1534365 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[C:24]([O:26]C)=[O:25])(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-].[K+]>C(O)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[C:24]([OH:26])=[O:25])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11726157HCID 11726157, compound

Product 1

HCID 9975044HCID 9975044, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-butyryl-4-(2-methylphenylamino)quinoline-8-carboxylate (0.3 g, 0.8 mmol) and potassium hydroxide (0.06 g, 1 mmol) were dissolved in ethanol (5 ml) and refluxed for 30 minutes, then the ethanol was evaporated, the product dissolved in water, the solution neutralised with dilute hydrochloric acid, and the solid filtered off and washed with water. Recrystallisation from ethanol gave 3-butyryl-4-(2-methyl-phenylamino)quinoline-8-carboxylic acid (0.18 g, 62%), m.p. 179-180°.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customthe ethanol was evaporated
  3. dissolutionthe product dissolved in water
  4. filtrationthe solid filtered off
  5. washwashed with water
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-1b78a6a912724a239224357fabdef65d
Source dataset
uspto-grants-1992_02
Patent number
US05089498

Reaction notes

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