Hydrochloric Acid → HCID 12423622, compound

HRID 1447684Notes

Reaction equation

HRID 1447684 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:18][C:17]3[C:12](=[C:13]([Cl:21])[C:14]([Cl:20])=[C:15]([OH:19])[CH:16]=3)[C:11]2=[O:22])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23](=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33]CC)=[O:32].[OH-].[Na+].Cl>CN(C)C=O.O>[O:22]=[C:11]1[C:12]2[C:17](=[CH:16][C:15]([O:19][CH2:30][C:31]([OH:33])=[O:32])=[C:14]([Cl:20])[C:13]=2[Cl:21])[CH2:18][C:10]1([CH3:23])[C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 86735779HCID 86735779, compound

Product 1

HCID 12423622HCID 12423622, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-methyl-2-(4-nitrophenyl-5-hydroxy-6,7-dichloro-1-indanone (4.4 g., 0.0126 mole), potassium carbonate (3.49 g., 0.0252 mole) and ethyl bromoacetate (4.21 g., 0.0252 mole) in dimethylformamide (150 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (150 ml.)-10 N sodium hydroxide solution (7.5 ml., 0.075 mole) and heated at 100° C. for 1.5 hours. The reaction mixture is added slowly to water (1 l.)-12 N hydrochloric acid (15 ml.) to precipitate 2.44 g. of [1-oxo-2-methyl-2-(4-nitrophenyl)-6,7-dichloro-5-indanyloxy]acetic acid which melts at 202°-205° C. after crystallization from nitromethane.

Workup

  1. temperatureis warmed at 55°-60° C. for 3 hours
  2. customto precipitate 2.44 g
  3. customof [1-oxo-2-methyl-2-(4-nitrophenyl)-6,7-dichloro-5-indanyloxy]acetic acid which melts at 202°-205° C. after crystallization from nitromethane

Sources & evidence

ORD record
ord-f190a1fcca0b4d4c8d2a299c806ee917
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

Loading…