Methylamine → N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine

HRID 2383129Notes

Reaction equation

HRID 2383129 reaction equation
[CH3:1][NH2:2].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]2Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]2[NH:2][CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 670509926-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 67051077N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Methylamine (available as a 40% solution in water, 21 mL, 0.25 mol) was added to a suspension of 6-benzyloxy-4-chloro-3-nitroquinoline (13.74 g, 43.65 mmol) in distilled water (300 mL), and the reaction was stirred at 100° C. for 1.5 hours. The reaction was allowed to cool to ambient temperature and stirred for three hours. A precipitate formed, which was isolated by filtration, washed with distilled water (3×), and recrystallized from 2-propanol (44.2 mL/g). The crystals were isolated by filtration and washed with cold hexanes (2×100 mL) to provide 11.36 g of N-(6-benzyloxy-3-nitroquinolin-4-yl)-N-methylamine as orange crystals.

Workup

  1. temperatureto cool to ambient temperature
  2. stirringstirred for three hours
  3. customA precipitate formed
  4. customwhich was isolated by filtration
  5. washwashed with distilled water (3×)
  6. customrecrystallized from 2-propanol (44.2 mL/g)
  7. customThe crystals were isolated by filtration
  8. washwashed with cold hexanes (2×100 mL)

Sources & evidence

ORD record
ord-65527ff9aa8b4d7cbccbaea8e90db8aa
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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