Hydrochloric Acid → [1-Oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid sodium salt

HRID 839705Notes

Reaction equation

HRID 839705 reaction equation
Cl.[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]([O:18]CC)=[O:17])=[C:9]([Cl:13])[C:10]=2[Cl:12])[CH2:5][C:4]1([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][NH2:29])=[CH:24][CH:23]=1)[CH3:21].C(=O)(O)[O-].[Na+:34].C(O)C.Cl>O>[Na+:34].[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]([O-:18])=[O:17])=[C:9]([Cl:13])[C:10]=2[Cl:12])[CH2:5][C:4]1([C:22]1[CH:23]=[CH:24][C:25]([CH2:28][NH2:29])=[CH:26][CH:27]=1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 20378231Ethyl[1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetate hydrochloride

Product 1

HCID 70588756[1-Oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid sodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl [1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetate hydrochloride (1.57 g., 0.0034 mole), sodium bicarbonate (1.15 g., 0.0136 mole), absolute ethanol (50 ml.) and water (50 ml.) are combined and heated at reflux for 1.5 hours leaving a solution which is filtered, then neutralized with 1N hydrochloric acid (10.26 ml., 0.01026 mole) to precipitate 900 mg. of [1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid sodium salt which melts at 270°-271° C. after drying.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. customleaving a solution which
  4. filtrationis filtered
  5. customto precipitate 900 mg
  6. dry with materialof [1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid sodium salt which melts at 270°-271° C. after drying

Sources & evidence

ORD record
ord-42c46442e98547bfab74bda035c5d2c5
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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