3-Isopropoxybenzoic acid → (6-Chloro-1,2-dihydro-2-methyl-1-oxo-4-phenylisoquinolin-3-yl)methyl N-(3-isopropoxyphenyl)carbamate

HRID 260457Notes

Reaction equation

HRID 260457 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([N:11]=[C:12]=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(OC1C=C(C=CC=1)C(O)=O)(C)C.[Cl:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34](=[O:38])[N:33]([CH3:39])[C:32]([CH2:40][OH:41])=[C:31]2[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1C=CC=CC=1>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:13])[O:41][CH2:40][C:32]2[N:33]([CH3:39])[C:34](=[O:38])[C:35]3[C:30]([C:31]=2[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:29][C:28]([Cl:27])=[CH:37][CH:36]=3)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5867093-Isopropoxybenzoic acidHCID 153374053-IsopropoxyphenylisocyanateHCID 224013336-Chloro-3-(hydroxymethyl)-2-methyl-4-phenylisoquinolin-1(2H)-one

Product 1

HCID 22401377(6-Chloro-1,2-dihydro-2-methyl-1-oxo-4-phenylisoquinolin-3-yl)methyl N-(3-isopropoxyphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-isopropoxyphenylisocyanate in benzene (25 ml) [prepared from 3-isopropoxybenzoic acid (405 mg) in substantially the same manner as described in Method A of Example 1] was added 6-chloro-1,2-dihydro-3-hydroxymethyl-2-methyl-1-oxo-4-phenylisoquinoline (Reference Example 3) (300 mg), and the mixture was heated for 1.5 hours under reflux. The solvent was distilled off. To the residue was added ethyl acetate. This mixture was washed with water, dilute hydrochloric acid, water, an aqueous solution of sodium carbonate and water, successively, followed by drying (Na2SO4). The solvent was distilled off to leave the title compound as colorless crystals (435 mg).

Workup

  1. temperaturethe mixture was heated for 1.5 hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off
  4. additionTo the residue was added ethyl acetate
  5. washThis mixture was washed with water, dilute hydrochloric acid, water
  6. dry with materialby drying (Na2SO4)
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-cda1faed32944b6da5028aff07b484d6
Source dataset
uspto-grants-1996_06
Patent number
US05527811

Reaction notes

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