Ammonium formate → 4-[3-(Morpholin-4-yl)quinoxalin-6-yl]benzene-1,2-diamine

HRID 524374Notes

Reaction equation

HRID 524374 reaction equation
C([O-])=O.[NH4+].C([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[CH:24][C:23]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[N:22]3)=[CH:15][C:14]=1[N+:35]([O-])=O)C1C=CC=CC=1>CO.O.[Pd]>[N:29]1([C:23]2[CH:24]=[N:25][C:26]3[C:21]([N:22]=2)=[CH:20][C:19]([C:16]2[CH:15]=[C:14]([NH2:35])[C:13]([NH2:12])=[CH:18][CH:17]=2)=[CH:28][CH:27]=3)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 67035007N-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-2-nitroaniline

Product 1

HCID 670350024-[3-(Morpholin-4-yl)quinoxalin-6-yl]benzene-1,2-diamineYield 55.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Pd/C (120 mg, 1.13 mmol) and ammonium formate (857 mg, 13.6 mmol) were added to a suspension of N-benzyl-4-[3-(morpholin-4-yl)quinoxalin-6-yl]-2-nitroaniline (1.2 g, 2.7 mmol) in MeOH (120 mL) and water (0.12 mL). The reaction mixture was refluxed for 4 h, then filtered over Celite. After removal of solvent the residue was purified (silica gel, Hexane/EtOAc: 10%->100% EtOAc) giving rise to 480 mg (48%) of the desired product.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. filtrationfiltered over Celite
  3. customAfter removal of solvent the residue
  4. customwas purified (silica gel, Hexane/EtOAc: 10%->100% EtOAc)

Sources & evidence

ORD record
ord-f4627ff0546a484b972b5d64f1fdd1af
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

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