Isobutylamine → 4-Quinolinamine, 2-chloro-N-(2-methylpropyl)-3-nitro-

HRID 1450688Notes

Reaction equation

[CH3:1][CH:2]([CH3:5])[CH2:3][NH2:4].[Cl:6][C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15](Cl)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1>C(N(CC)CC)C>[Cl:6][C:7]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:4][CH2:3][CH:2]([CH3:5])[CH3:1])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2-Methylpropylamine (0.5 mL) was added to a suspension of 2,4-dichloro-3-nitroquinoline (1 g) and triethylamine (15 mL) at 40° C. over a period of 40 min. The solution was then heated at 70° C. for 1 h. The triethylamine and 2-methylpropylamine were removed by distillation and the residue was slurried for 1 h in aqueous 1N HCl. The solid product 2-chloro-N-(2-methylpropyl)-3-nitro-4-quinolinamine was collected by filtration, washed with water and recrystallized from petroleum ether.

Workup

customThe triethylamine and 2-methylpropylamine were removed by distillation
filtrationThe solid product 2-chloro-N-(2-methylpropyl)-3-nitro-4-quinolinamine was collected by filtration
washwashed with water
customrecrystallized from petroleum ether

Sources & evidence

ORD record: ord-a97448424c5b498db2acfb6fb95fcf18
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05602256

Reaction notes

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