Methanol → HCID 12802824, compound

HRID 1833387Notes

Reaction equation

HRID 1833387 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])=[CH:10][C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[C:26](=O)(O)[O-].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]([CH3:22])[C:19]([O:21][CH3:26])=[O:20])=[CH:10][C:9]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 12802755HCID 12802755, compound

Product 1

HCID 12802824HCID 12802824, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of α(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid (0.5g.), methanol (5ml.) and concentrated sulphuric acid (4 drops) was heated under reflux for six hours. The mixture was then poured into water (10 ml.), and the resulting mixture was neutralised with sodium bicarbonate solution. The mixture was extracted with ethyl acetate (3 × 5 ml.) and the combined extracts were washed successively with sodium bicarbonate solution (5 ml.) and water (5 ml.), and then dried with sodium sulphate. The solvent was evaporated in vacuo and the residue crystallised from cyclohexane to give methyl α-(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionate m.p. 90°-92.5° C, in 74% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for six hours
  3. extractionThe mixture was extracted with ethyl acetate (3 × 5 ml.)
  4. washthe combined extracts were washed successively with sodium bicarbonate solution (5 ml.) and water (5 ml.)
  5. dry with materialdried with sodium sulphate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue crystallised from cyclohexane

Sources & evidence

ORD record
ord-a6e95c3b74474324b7fa79645379db30
Source dataset
uspto-grants-1978_01
Patent number
US04066651

Reaction notes

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