N,N-Diethylethylenediamine → 2H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

HRID 1679071Notes

Reaction equation

HRID 1679071 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)[CH3:2].[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH2:28])[CH3:24]>C(O)=O>[ClH:13].[CH2:1]([O:3][C:4]([C:5]1[N:28]([CH2:27][CH2:26][N:25]([CH2:29][CH3:30])[CH2:23][CH3:24])[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]2[C:7]=1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9]2)=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 54162441o-Benzoyl-p-chloro-phenylglyoxylic acid ethyl ester

Product 1

HCID 30458932H-Isoindole-1-carboxylic acid, 5-chloro-2-(2-(diethylamino)ethyl)-3-phenyl-, ethyl ester, monohydrochloride

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In a manner analogous to that described in Example 19, from 0.95 g. of o-benzoyl-p-chloro-phenylglyoxylic acid ethyl ester, 1.05 g. of 2-diethylaminoethylamine and 0.83 g. of formic acid, there is obtained 5-chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 248°-250° C. (decomposition).

Sources & evidence

ORD record
ord-6d27f15b1eb040349c969079d0a7b1ca
Source dataset
uspto-grants-1978_03
Patent number
US04077978

Reaction notes

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