Hydrochloric Acid → Ethyl[1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetate hydrochloride

HRID 2052058Notes

Reaction equation

HRID 2052058 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)=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26]C(=O)CCl)=[CH:21][CH:20]=1)[CH3:18].Cl.[CH2:32]([OH:34])[CH3:33]>>[ClH:11].[CH2:32]([O:34][C:15](=[O:17])[CH2:14][O:13][C:7]1[CH:6]=[C:5]2[C:10](=[C:9]([Cl:11])[C:8]=1[Cl:12])[C:2](=[O:1])[C:3]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][NH2:26])=[CH:23][CH:24]=1)([CH3:18])[CH2:4]2)[CH3:33]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12423624{1-Oxo-2-[4-(2-chloroacetamidomethyl)phenyl]-2-methyl-6,7-dichloro-5-indanyloxy}acetic acid

Product 1

HCID 20378231Ethyl[1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetate hydrochloride

Conditions

Temperature
5 °C

Procedure

{1-Oxo-2-[4-(2-chloroacetamidomethyl)phenyl]-2-methyl-6,7-dichloro-5-indanyloxy}acetic acid (2.0 g., 0.004 mole), absolute ethanol (20 ml.) and 12 N hydrochloric acid (7 ml.) are combined and heated at reflux for 3 hours. On cooling to 5° C. 1.14 g. of ethyl[1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetate hydrochloride precipitates and melts at 211°-213° C. after crystallization from ethanol.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customof ethyl[1-oxo-2-(4-aminomethylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetate hydrochloride precipitates
  4. custommelts at 211°-213° C. after crystallization from ethanol

Sources & evidence

ORD record
ord-e3104a95d683437d89259fec5871cd81
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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