Diethylamine → N,N-Diethyl-1-(4-methylphenyl)isoquinoline-3-carboxamide

HRID 615389Notes

Reaction equation

HRID 615389 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=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 132723901-(4-Methylphenyl)isoquinoline-3-carboxylic acid

Product 1

HCID 13272365N,N-Diethyl-1-(4-methylphenyl)isoquinoline-3-carboxamideYield 53.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Operations are carried out as for Example 7, starting from 5 g of 1-(4-methylphenyl) isoquinoline 3-carboxylic acid, 2.18 g of triethylamine, 2.39 g of ethyl chloroformate and 1.83 g of diethylamine in 190 ml of chloroform. 3.25 g of N,N-diethyl 1-(4-methylphenyl) isoquinoline 3-carboxamide melting at 113° C., are obtained.

Sources & evidence

ORD record
ord-f4e4ff75bc4249a397f6b34a6a94c111
Source dataset
uspto-grants-1985_02
Patent number
US04499094

Reaction notes

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