Hydrogen chloride-ethyl acetate → 2-(4-carboxybenzyl)-6-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750177Notes

Reaction equation

HRID 750177 reaction equation
Cl.C(OCC)(=O)C.[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39]C(C)(C)C)=[O:38])=[CH:33][CH:32]=2)[C:14](=[O:29])[C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][C:18]([CH3:28])=[CH:17][CH:16]=2)=[O:11]>>[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]([OH:39])=[O:38])=[CH:35][CH:36]=2)[C:14](=[O:29])[C:15]2[C:20]([C:21]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:19][C:18]([CH3:28])=[CH:17][CH:16]=2)=[O:11]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 691566112-(4-tert-butoxycarbonylbenzyl)-6-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691578052-(4-carboxybenzyl)-6-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 92.6%

Procedure

To a 4N-hydrochloric acid-ethyl acetate solution (6 ml) was added 2-(4-tert-butoxycarbonylbenzyl)-6-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (220 mg) at room temperature, and the mixture was stirred for 6 hrs. The reaction mixture was concentrated under reduced pressure, and the obtained residue was crystallized from ethyl acetate-hexane to give the title compound (180 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b69982f1daed42819d4a97106b4fe84e
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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