Water → HCID 12802755, compound

HRID 1448828Notes

Reaction equation

HRID 1448828 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)P(N(C)C)(N(C)C)=O.[OH-].[Na+]>[CH2:17]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:11][C:2]1=[O:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7498Benzyl BromideHCID 20375604HCID 20375604, compound

Product 1

HCID 12802755HCID 12802755, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 12679HexamethylphosphoramideSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

α-(1,2-Dihydro-2-oxoquinol-4-yl)propionic acid (217 mg.) was dissolved in a mixture of hexamethylphosphoramide (2 ml.) and 2 N-sodium hydroxide (2 ml.). A solution of benzyl bromide (0.528 ml.) in hexamethylphosphoramide (2 ml.) was added dropwise to the stirred solution during 2 hours. The mixture was then poured into water (10 ml.), and the resulting mixture washed with chloroform (3×5 ml.). The aqueous solution was acidified to pH 1 with concentrated hydrochloric acid, and the resulting mixture was filtered and the white solid residue washed with water and dried in vacuo over phosphorus pentoxide. The solid was crystallised from ethanol to give α-(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid, m.p. 178°-180° C. (decomposition), in 39% yield.

Workup

  1. washthe resulting mixture washed with chloroform (3×5 ml.)
  2. filtrationthe resulting mixture was filtered
  3. washthe white solid residue washed with water
  4. dry with materialdried in vacuo over phosphorus pentoxide
  5. customThe solid was crystallised from ethanol

Sources & evidence

ORD record
ord-0e26d333d04e4cf186f81610c5d91c8b
Source dataset
uspto-grants-1980_02
Patent number
US04187310

Reaction notes

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