Benzoic acid, 3-methoxy-2-nitro-, methyl ester → Methyl 2-amino-3-methoxybenzoate

HRID 463065

Reaction equation

HRID 463065 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:13]([O-])=O)=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]>C1(C)C=CC=CC=1.[Pt]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[NH2:13]

Participants

4

Reactant 1

HCID 79195Benzoic acid, 3-methoxy-2-nitro-, methyl ester

Product 1

HCID 602320Methyl 2-amino-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

One hundred thirty-three grams (0.63 mol) of methyl 3-methoxy-2-nitro-benzoate are dissolved in 1000 ml of toluene and hydrogenated in an autoclave at ambient temperature and under a hydrogen pressure of 5 bar in the presence of platinum over a period of two hours. The catalyst is removed by filtration, the residue is dried with sodium sulfate, and the toluene is distilled off in vacuo. Oil, RF value: 0.8 [silica gel plate; chloroform/acetone (9:1)],

Workup

  1. customhydrogenated in an autoclave at ambient temperature and under a hydrogen
  2. customof two hours
  3. customThe catalyst is removed by filtration
  4. dry with materialthe residue is dried with sodium sulfate
  5. distillationthe toluene is distilled off in vacuo

Sources & evidence

ORD record
ord-b6f69015d892488a930568c8d1363b2b
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Linked notes

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