Methyl 2-hydroxy-3-nitrobenzoate → Methyl 3-amino-2-hydroxybenzoate

HRID 259262Notes

Reaction equation

HRID 259262 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[C:7]([N+:11]([O-])=O)[CH:8]=[CH:9][CH:10]=1)[OH:6].[H][H]>[Ni].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)[OH:6]

Participants

5

Reactant 2

HCID 596904Methyl 2-hydroxy-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

One-tenth mol of methyl-m-nitrosalicylate is dissolved in 250 ml. of ethyl acetate and 10 gms. of Raney nickel added. The mixture is placed in a suitable container to permit pressure hydrogenation and hydrogen gas is passed into the solution. When the gas pressure reaches 10 pounds psi. at 80° C., the mixture is agitated and when the absorption of hydrogen has reached equilibrium, it is shaken for four hours and cooled. The mixture is filtered and the formed methyl-m-aminosalicylat is isolated by distillation and is obtained as an oily compound which distills at 126° C. at 2 mm. Hg. pressure.

Workup

  1. customwhen the absorption of hydrogen
  2. stirringis shaken for four hours
  3. temperaturecooled
  4. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-b1082a3ab1a24bb0bd56118988e677f8
Source dataset
uspto-grants-1977_07
Patent number
US04036951

Reaction notes

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