Diethylamine → 1-(3-Chlorophenyl)-N,N-diethylisoquinoline-3-carboxamide

HRID 615388Notes

Reaction equation

HRID 615388 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([C:18]([OH:20])=O)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22].ClC(OCC)=O.C(NCC)C>C(Cl)(Cl)Cl>[CH2:21]([N:23]([CH2:24][CH3:25])[C:18]([C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[C:12]([CH:11]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:20])[CH3:22]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 132723891-(3-Chlorophenyl)isoquinoline-3-carboxylic acid

Product 1

HCID 132723641-(3-Chlorophenyl)-N,N-diethylisoquinoline-3-carboxamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Operations are carried out as for Example 7, starting with 1.7 g of 1-(3-chlorophenyl) isoquinoline 3-carboxylic acid, 0.69 g of triethylamine, 0.74 g of ethyl chloroformate and 0.56 g of diethylamine in 60 ml of chloroform. 1.45 g of N,N-diethyl 1-(3-chlorophenyl) isoquinoline 3-carboxamide melting at 116° C., are obtained.

Sources & evidence

ORD record
ord-ab0b9e72187949fc9176c618ed1c9862
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Reaction notes

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