HCID 12531249, compound → HCID 53875341, compound

HRID 261361Notes

Reaction equation

HRID 261361 reaction equation
[C:1]([C:4](=[O:17])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:6])([OH:3])=[O:2]>[Pd].CO>[C:1]([C:4](=[O:17])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)=[O:6])([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 12531249HCID 12531249, compound

Product 1

HCID 53875341HCID 53875341, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.2 g. (0.005 mol) of N-(2-carboxy-2-oxoacetyl)-3-nitroaniline in 60 ml. of methanol was hydrogenated over 200 mg. of 10% palladium-on-carbon at 50 psi. When the theoretical amount of hydrogen had been absorbed the reduction was stopped, 40 ml. of 5% aqueous sodium bicarbonate solution was added and the catalyst filtered. The filtrate was evaporated to approximately 50 ml., acidified with 3N hydrochloric acid to pH 2 and the resulting precipitate filtered, washed with water and dried to give N-(2-carboxy-2-oxoacetyl)-1,3-phenylene diamine, m.p. 246° C.

Workup

  1. customWhen the theoretical amount of hydrogen had been absorbed the reduction
  2. additionof 5% aqueous sodium bicarbonate solution was added
  3. filtrationthe catalyst filtered
  4. customThe filtrate was evaporated to approximately 50 ml
  5. filtrationthe resulting precipitate filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ab17bf61ea7145b0a0a0cf275c6ed1ef
Source dataset
uspto-grants-1979_08
Patent number
US04165365

Reaction notes

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