4-chloroquinolin-3-amine → HCID 86625942, compound

HRID 415495Notes

Reaction equation

HRID 415495 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH2:12].[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][N:22]=2)[N:17]=[CH:16][C:15]=1[NH2:24]>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH-:12].[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][N:22]=2)[N:17]=[CH:16][C:15]=1[NH-:24]

Participants

4

Reactant 2

HCID 8173324-chloroquinolin-3-amineHCID 666199614-Chloro-1,5-naphthyridin-3-amine

Product 2

HCID 86625942HCID 86625942, compoundHCID 86625943HCID 86625943, compound

Procedure

In step (1) of Reaction Scheme I, a 4-chloroquinolin-3-amine or 4-chloro[1,5]naphthyridin-3-amine of Formula XX is reacted with an acid halide of Formula Hal-Z—CH2—C(O)—Hal to provide an N-(4-chloroquinolin-3-yl)amide or N-(4-chloro[1,5]naphthyridin-3-yl)amide of Formula XXI. The reaction can be carried out by heating a solution of a compound of Formula XX and the acid halide in a suitable solvent such as 1,2-dichloroethane. Some acid chlorides of Formula Hal-Z—CH2—C(O)—Hal are commercially available; others can be prepared using conventional synthetic methods. Some 4-chloroquinolin-3-amines and 4-chloro[1,5]naphthyridin-3-amines of Formula XX are known. Others can be prepared using conventional synthetic methods; for example, by reduction of known 4-chloro-3-nitroquinolines and 4-chloro-3-nitro[1,5]naphthyridines.

Workup

  1. customIn step (1) of Reaction Scheme I

Sources & evidence

ORD record
ord-d5a88e4ec13f445e8fe622339e34cee5
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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