Thionyl Chloride → N-(4-chlorobutyl)-3-nitroquinolin-4-amine

HRID 497900Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18]O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].S(Cl)([Cl:22])=O>>[Cl:22][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 121061814-[(3-Nitroquinolin-4-yl)amino]butan-1-ol

Product 1

HCID 22320535N-(4-chlorobutyl)-3-nitroquinolin-4-amineYield 99.6%

Procedure

Using the general method of Example 19 Part A, 4-[(3-nitroquinolin-4-yl)amino]butan-1-ol (120 g, 0.459 mol) was chlorinated with thionyl chloride (109 g, 0.919 mol) to provide 127.9 g of N-(4-chlorobutyl)-3-nitroquinolin-4-amine as a yellow powder.

Sources & evidence

ORD record: ord-b00aedf87a2a42baa4e473195df8a52c
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949649B2

Reaction notes

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