Benzoic acid, 4,5-dimethoxy-2-nitro-, methyl ester → Methyl 4,5-dimethoxyanthranilate

HRID 1075765Notes

Reaction equation

HRID 1075765 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10]([N+:15]([O-])=O)=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]>[Ni].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:10]([NH2:15])=[CH:11][C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 117867Benzoic acid, 4,5-dimethoxy-2-nitro-, methyl ester

Product 1

HCID 611144Methyl 4,5-dimethoxyanthranilateYield 97.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In an hydrogenating autoclave, there are placed 144 g of methyl 3,4-dimethoxy-6-nitro-benzoate, 300 ml of tetrahydrofuran and 3 coffee spoonfuls of Raney nickel. Hydrogenation occurs at about 35°C. In 20 minutes, the pressure drop is 80 kg. It is cooled, the nickel filtered, and the tetrahydrofuran removed under vacuum. There are obtained 123 g (97%) of methyl 3,4-dimethoxy-6-aminobenzoate. (m.p.: 130°C).

Workup

  1. customoccurs at about 35°C
  2. temperatureIt is cooled
  3. filtrationthe nickel filtered
  4. customthe tetrahydrofuran removed under vacuum

Sources & evidence

ORD record
ord-fabfc5445ebb48ad9ce453bdad101005
Source dataset
uspto-grants-1976_05
Patent number
US03954748

Reaction notes

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