Diethyl Carbonate → Ethyl 3-phenyl-2H-isoindole-1-carboxylate

HRID 372302Notes

Reaction equation

HRID 372302 reaction equation
CN1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][CH2:4][C:3]1=[O:19].[CH2:20]([O:22]C(=O)OCC)[CH3:21]>>[CH2:20]([O:22][C:3]([C:4]1[NH:5][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=[O:19])[CH3:21]

Participants

3

Reactant 2

HCID 7766Diethyl CarbonateHCID 6138431-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one

Product 1

HCID 53760678Ethyl 3-phenyl-2H-isoindole-1-carboxylate

Procedure

The starting material can be prepared from 1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one and diethylcarbonate in a manner analogous to that described in Example 1. After recrystallization from ethanol, there is obtained 3-phenylisoindole-1-carboxylic acid ethyl ester; m.p. 144°-147° C. (decomposition).

Workup

  1. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-7aa0a88c99e44535836e14d20dc2a662
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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