Chloroacetone → HCID 19825008, compound

HRID 727783Notes

Reaction equation

HRID 727783 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][CH2:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:10](=[O:21])[CH:9]=3.Cl[CH2:25][C:26](=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][CH2:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:25][C:26](=[O:28])[CH3:27])=[CH:16][CH:15]=1)[C:10](=[O:21])[CH:9]=3

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 14987013HCID 14987013, compound

Product 1

HCID 19825008HCID 19825008, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5 g of 9-fluoro-2-(4-hydroxyphenyl)-5,6-dihydrobenzo[h]cinnolin-3(2H)-one, 4.5 g of chloroacetone, 8.8 g of potassium carbonate and 100 ml of acetone is heated under reflux for 9 hours. After acetone is distilled off, water and isopropyl ether are added to the residue. The resultant crystals are collected and washed with ethanol to give 5 g of crude 9-fluoro-2-[4-(2-oxopropoxy)phenyl]-5,6-dihydrobenzo[h]cinnolin-3(2H)-one, which is subjected to the following reaction without purification.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 9 hours
  3. distillationAfter acetone is distilled off
  4. additionwater and isopropyl ether are added to the residue
  5. customThe resultant crystals are collected
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-71112e9599ed43a890eb392463fe469f
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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