Water → HCID 12423623, compound

HRID 1447685Notes

Reaction equation

HRID 1447685 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.)-36 N 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.), 10 N 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 6 N 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-3dab01005d3b48089a6ad195f521b9d7
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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