5-Nitro-6-phenoxyphthalide → 5-Amino-6-phenoxyphthalide

HRID 648225Notes

Reaction equation

HRID 648225 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9](=[O:10])[O:8][CH2:7]2)([O-])=O>CO.O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9](=[O:10])[O:8][CH2:7]2

Participants

5

Reactant 1

HCID 130692025-Nitro-6-phenoxyphthalide

Product 1

HCID 130692065-Amino-6-phenoxyphthalideYield 67.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

950 mg of 5-nitro-6-phenoxyphthalide in 120 ml of methanol and 30 ml of tetrahydrofuran is hydrogenated in the presence of 2 g of Raney nickel within 3 hours at 20 bar, filtered, and concentrated. From methanol, 570 mg of 5-amino-6-phenoxyphthalide is obtained, mp 205°-206.5° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-aa21e350c6104241979c4306d6cb88be
Source dataset
uspto-grants-1983_10
Patent number
US04411910

Reaction notes

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