2-(3-Methoxy-2-nitrophenyl)-4H-chromen-4-one → 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one

HRID 260087Notes

Reaction equation

HRID 260087 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:20]([O-])=O)=[C:5]([C:9]2[O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[CH:14]=2)[CH:6]=[CH:7][CH:8]=1>CO.C1COCC1.[Ni]>[NH2:20][C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[O:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13](=[O:15])[CH:14]=1

Participants

5

Reactant 1

HCID 224024972-(3-Methoxy-2-nitrophenyl)-4H-chromen-4-one

Product 1

HCID 47132-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-oneYield 58.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Methoxy-2-nitrophenyl)-4-oxo-4H-[1]benzopyran (1.73 g, 5.8 mmol) in methanol (50 mL) and THF (50 mL) is hydrogenated under pressure with RaNi (0.5 g). The solution is concentrated under reduced pressure and recrystallized from toluene to yield 2-(2-amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran (900 mg, 58%) as a solid. 1H NMR (DMSO): δ8.07 (1H, d, J=8.0 Hz), 7.83 (1H, t, J=6.9 Hz), 7.70 (1H, d, J=7.7 Hz), 7.51 (1H, t, J=7.0 Hz), 7.09 (1H, d, J=8.0 Hz), 7.00 (1H, d, J=7.0 Hz), 6.71 (1H, t, J=8.0 Hz), 6.56 (1H, s), 5.30 (2H, s), 3.85 (3H, s).

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. customrecrystallized from toluene

Sources & evidence

ORD record
ord-b3bb126a7d714748a9b67c6420829914
Source dataset
uspto-grants-1996_06
Patent number
US05525625

Reaction notes

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