Hydrochloric Acid → HCID 20378219, compound

HRID 1447693Notes

Reaction equation

HRID 1447693 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:22])[CH2:17][C:16]3[C:11](=[C:12]([Cl:20])[C:13]([Cl:19])=[C:14]([OH:18])[CH:15]=3)[C:10]2=[O:21])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33]CC)=[O:32].[OH-].[Na+].Cl>CN(C)C=O.O>[O:21]=[C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:18][CH2:30][C:31]([OH:33])=[O:32])=[C:13]([Cl:19])[C:12]=2[Cl:20])[CH2:17][C:9]1([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH3:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20378216HCID 20378216, compound

Product 1

HCID 20378219HCID 20378219, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-(4-cyanophenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (1.8 g., 0.0054 mole), potassium carbonate (1.5 g., 0.0109 mole) and ethyl bromoacetate (1.8 g., 0.0109 mole) in dimethylformamide (60 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (60 ml.)-10 N sodium hydroxide solution (3 ml., 0.03 mole) and heated at 100° C. for 1.5 hours. The reaction mixture is added slowly to ice-water (300 ml.)-12 N hydrochloric acid (5 ml.) to precipitate 160 mg. of [1-oxo-2-(4-cyanophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 184°-5° C. after crystallization from acetic acid: water, 1:1.

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. customto precipitate 160 mg
  3. customof [1-oxo-2-(4-cyanophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 184°-5° C. after crystallization from acetic acid

Sources & evidence

ORD record
ord-0f638d79618d43599a00ec2e53d1b625
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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