Water → 6-bromo-N-(4-methyloxan-4-yl)-3-nitroquinolin-4-amine

HRID 1486941Notes

Reaction equation

HRID 1486941 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2Cl.Cl.[CH3:17][C:18]1([NH2:24])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[NH:24][C:18]1([CH3:17])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 184373724-Methyloxan-4-amine hydrochlorideHCID 219841286-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 1184987426-bromo-N-(4-methyloxan-4-yl)-3-nitroquinolin-4-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-4-chloro-3-nitroquinoline (1 g, 3.48 mmol), 4-methyltetrahydro-2H-pyran-4-amine hydrochloride (1.055 g, 6.96 mmol) and triethylamine (1.939 mL, 13.91 mmol) in DMF (10 mL) was heated to 100° C. for 1 h in a sealed tube in the microwave reactor. The mixture was allowed to cool then poured into stirred water (50 mL) and the resulting yellow precipitate was collected by filtration and dried under vacuum to afford the desired material (1.070 g, 84%) as a yellow solid. This was used without further purification. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 1.40 (3H, s), 1.78 (2H, dt), 1.89 (2H, ddd), 3.51-3.64 (4H, m), 7.80 (1H, s), 7.91 (1H, d), 8.01 (1H, dd), 8.48 (1H, d), 9.18 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=366, 368.

Workup

  1. temperatureto cool
  2. additionthen poured
  3. filtrationthe resulting yellow precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-fb945c23ef2f40eb8b0678b0b8b13e85
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

Loading…