Diethyl Carbonate → Ethyl 3-[3-(trifluoromethyl)phenyl]-2H-isoindole-1-carboxylate

HRID 372312Notes

Reaction equation

HRID 372312 reaction equation
CN1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:17][CH:18]=2)=[N:5][CH2:4][C:3]1=[O:23].[CH2:24]([O:26]C(=O)OCC)[CH3:25].[H-].[Na+]>>[CH2:24]([O:26][C:3]([C:4]1[NH:5][C:6]([C:13]2[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:17][CH:18]=2)=[C:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=[O:23])[CH3:25]

Participants

4

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 20364766HCID 20364766, compound

Product 1

HCID 54020357Ethyl 3-[3-(trifluoromethyl)phenyl]-2H-isoindole-1-carboxylate

Procedure

According to the procedure described in Example 1, 1,3-dihydro-1-methyl-5-(α, α, α-trifluoro-m-tolyl)-2H-1,4-benzodiazepin-2-one is reacted with diethylcarbonate in the presence of sodium hydride, and there is obtained 3-(α, α, α-trifluoro-m-tolyl)-isoindole-1-carboxylic acid ethyl ester, having a melting point of 155°-157° C. Recrystallization from ethanol does not increase the melting point.

Sources & evidence

ORD record
ord-29e03d32da1b451da60a8be7a58bbd9f
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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