HCID 66664617, compound → HCID 68285181, compound

HRID 2174940Notes

Reaction equation

HRID 2174940 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-])=O)=[C:5]2[NH:15][C:16]1[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1.[H][H]>C1COCC1.CO.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[NH:15][C:16]1[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 66664617HCID 66664617, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 68285181HCID 68285181, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

6-bromo-N-(6-methoxypyridin-3-yl)-3-nitroquinolin-4-amine (compound of step 2, 13.3 mmol) was hydrogenated using Raney-Ni (1 g) in THF-MeOH [(1:1), 50 mL] under 40 psi of hydrogen for 4 h at RT. After completion of the reaction, the reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated and purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 8.59 (s, 1H), 7.93 (d, J=2.1 Hz, 1H), 7.78 (d, J=8.7 Hz, 3H), 7.47 (dd, J=2.1, 9.0 Hz, 2H), 6.93 (dd, J=3.0, 8.7 Hz, 1H), 6.65 (d, J=9.0 Hz, 1H), 5.42 (s, 2H), 3.85 (s, 3H); MS (m/z): 345.0 (M+1)+.

Workup

  1. customfor 4 h
  2. customat RT
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered through celite
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated
  7. custompurified (silica gel column, MeOH/CHCl3 as eluent)

Sources & evidence

ORD record
ord-673e3b4168c24bf388dca37bc98a3868
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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