Water → HCID 12802755, compound

HRID 1390291Notes

Reaction equation

HRID 1390291 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 2N-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 acidifed 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-79c33b80912c4f339b12afe04cf18f8d
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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