Methanol → HCID 13234022, compound

HRID 1632506Notes

Reaction equation

HRID 1632506 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][C:11]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[C:10]([CH3:22])[CH:9]=2)=[O:5])C.CO.[OH-].[K+]>O>[C:17]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[CH3:22])[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15][C:14]2=[O:16])(=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 13234021HCID 13234021, compound

Product 1

HCID 13234022HCID 13234022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g of 6-butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester are heated under reflux for 4 hours together with 20 ml of methanol, 1.2 g of potassium hydroxide and 0.5 ml of water. The reaction mixture is concentrated to dryness by evaporation and taken up in water. The solution is acidified to pH 1 with 2N hydrochloric acid and filtered with suction. The product obtained by filtering with suction is thoroughly washed with water, resuspended in water, thoroughly triturated and stirred at room temperature for 5 hours, then filtered with suction, washed with water, and recrystallised twice from methanol. In this manner 6-butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid having a melting point of 255°-258° is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness by evaporation
  2. filtrationfiltered with suction
  3. customThe product obtained
  4. filtrationby filtering with suction
  5. washis thoroughly washed with water
  6. customthoroughly triturated
  7. filtrationfiltered with suction
  8. washwashed with water
  9. customrecrystallised twice from methanol

Sources & evidence

ORD record
ord-1e88f2aaa512468489a891a77eb7f75d
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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