Water → HCID 12423623, compound

HRID 839689Notes

Reaction equation

HRID 839689 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH3:27])[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1.S(=O)(=O)(O)O.[OH-].[Na+].O>C(O)C.[Pd]>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12423622HCID 12423622, compound

Product 1

HCID 12423623HCID 12423623, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[1-Oxo-2-methyl-2-(4-nitrophenyl)-6,7-dichloro-5-indanyloxy]acetic acid (6.11 g., 0.015 mole) in absolute ethanol (250 ml.)-36N sulfuric acid (2 ml.) is catalytically hydrogenated over 5% palladium on carbon (500 mg.) in a Parr apparatus. After one hour, the reaction mixture is filtered, then concentrated in vacuo to a 50 ml. volume. Water (200 ml.) is added to precipitate the ethyl ester which is hydrolyzed by refluxing in ethanol (200 ml.), 10N sodium hydroxide solution (4.5 ml., 0.045 mole) and water (100 ml.) for 1.5 hours. The reaction mixture is cooled, concentrated to 1/3 its volume, filtered, then neutralized with 6N hydrochloric acid to precipitate 1.09 g. of [1-oxo-2-(4-aminophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 235°-236° C. dec.

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationconcentrated in vacuo to a 50 ml
  3. additionWater (200 ml.) is added
  4. customto precipitate the ethyl ester which
  5. temperatureby refluxing in ethanol (200 ml.)
  6. temperatureThe reaction mixture is cooled
  7. concentrationconcentrated to 1/3 its volume
  8. filtrationfiltered
  9. customto precipitate 1.09 g

Sources & evidence

ORD record
ord-da67dfb982ec4e26a8a45fed6fe77bce
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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