Water → (7-Bromo-3-nitroquinolin-4-yl)isobutylamine

HRID 1907970Notes

Reaction equation

HRID 1907970 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25].O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:27][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 8471TriethylamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 21984282(7-Bromo-3-nitroquinolin-4-yl)isobutylamineYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 7-bromo-4-chloro-3-nitroquinoline (25.0 g, 87.0 mmol) in DMF (70 mL) was added triethylamine (18.2 mL, 130 mmol). A solution of iso-butylamine (9.50 mL, 95.7 mmol) in DMF (20 mL) was added dropwise. The viscous reaction mixture was stirred overnight at ambient temperature. Water (200 mL) was added and the mixture was stirred for 1 hour. A solid was isolated by filtration, washed with water, and dried in a vacuum oven overnight to yield 26.1 g of 7-bromo-N-(2-methylpropyl)-3-nitroquinolin-4-amine as a yellow powder.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customA solid was isolated by filtration
  3. washwashed with water
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-887bd905b4874b6ab5f5c7402cf1bbfb
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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