Cyclohexanemethylamine → (7-Bromo-3-nitroquinolin-4-yl)cyclohexylmethylamine

HRID 1818210Notes

Reaction equation

HRID 1818210 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](Cl)=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1>ClCCl>[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[N:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 68820944(7-Bromo-3-nitroquinolin-4-yl)cyclohexylmethylamineYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, cyclohexylmethylamine (40.9 mL, 315 mmol) was added dropwise to a solution of 7-bromo-4-chloro-3-nitroquinoline (30.0 g, 105 mmol) in dichloromethane (524 mL). The reaction was stirred for 18 hours at ambient temperature and then concentrated under reduced pressure. Water (200 mL) was added to the residue, and the mixture was stirred for three hours. Acetonitrile was added; a precipitate formed. The solid was isolated by filtration, dried under a flow of air for two hours, and recrystallized from acetonitrile to provide 24.0 g of (7-bromo-3-nitroquinolin-4-yl)cyclohexylmethylamine as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater (200 mL) was added to the residue
  3. stirringthe mixture was stirred for three hours
  4. additionAcetonitrile was added
  5. customa precipitate formed
  6. customThe solid was isolated by filtration
  7. customdried under a flow of air for two hours
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-e1259de9e2414103951076c93b55c075
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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