Hydrochloric Acid → Indacrinone

HRID 2052026Notes

Reaction equation

HRID 2052026 reaction equation
[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([OH:11])[CH:8]=2)[C:3]1=[O:14].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31]CC)=[O:30].[OH-].[K+].Cl>CN(C)C=O.O.CO>[O:14]=[C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:11][CH2:28][C:29]([OH:31])=[O:30])=[C:6]([Cl:12])[C:5]=2[Cl:13])[CH2:10][C:2]1([CH3:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 936906,7-Dichloro-5-hydroxy-2-methyl-2-phenylindan-1-one

Product 1

HCID 42266Indacrinone

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2-methyl-2-phenyl-5-hydroxy-6,7-dichloro-1-indanone (2.05 g., 0.0067 mole), potassium carbonate (1.85 g., 0.0134 mole) and ethyl bromoacetate (2.23 g., 0.0134 mole) in dimethylformamide (30 ml.) is warmed at 55°-60° C. for 3 hours, then treated with potassium hydroxide (0.97 g., 0.0147 mole) dissolved in a minimum amount of water in methanol (30 ml.) and heated on a steam bath for 21/2 hours. The reaction mixture is poured into water (500 ml.), acidified with 6 N hydrochloric acid and the precipitate collected after trituration with ether-petroleum ether and dried to give 1.31 g. of (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 168°-169° C. on crystallization from acetic acid:water, 1:1.

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. temperatureheated on a steam bath for 21/2 hours
  3. customthe precipitate collected after trituration with ether-petroleum ether
  4. customdried
  5. customto give 1.31 g
  6. customof (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 168°-169° C. on crystallization from acetic acid

Sources & evidence

ORD record
ord-8363513695bd4e2d9187c04a87766ee6
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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