HCID 22152173, compound → HCID 22152159, compound

HRID 1111309Notes

Reaction equation

HRID 1111309 reaction equation
[C:1]([NH:7][C:8]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])([O:3][CH:4]([CH3:6])[CH3:5])=[O:2].[H][H]>C(O)C.[C].[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([NH:7][C:1]([O:3][CH:4]([CH3:6])[CH3:5])=[O:2])[CH:16]=1

Participants

5

Reactant 2

HCID 22152173HCID 22152173, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22152159HCID 22152159, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution was prepared by dissolving 13.08 g of 2-carboisopropoxyamino-4-nitrobenzoic acid in 200 ml of ethyl alcohol and was mixed with 3 g of a 10% palladium-carbon catalyst. The resultant reaction mixture was stirred at room temperature in a hydrogen gas atmosphere for 2 hours. Then, the reaction mixture was filtered through a Celite filter and the catalyst on the Celite filter was washed with ethyl alcohol. The entire amount of the filtrate was collected, concentrated and dried under a reduced pressure, and the resultant crude product was recrystallized from an ethyl alcohol-water mixed solvent. The resultant 4-amino-2-carboisopropoxyaminobenzoic acid was obtained in a yield of 11.3 g and exhibited a melting point of 197° C.

Workup

  1. customA solution was prepared
  2. customThe resultant reaction mixture
  3. filtrationThen, the reaction mixture was filtered through a Celite
  4. filtrationfilter
  5. filtrationthe catalyst on the Celite filter
  6. washwas washed with ethyl alcohol
  7. customThe entire amount of the filtrate was collected
  8. concentrationconcentrated
  9. customdried under a reduced pressure
  10. customthe resultant crude product was recrystallized from an ethyl alcohol-water mixed solvent

Sources & evidence

ORD record
ord-580b767152684e1192bb1eada6bf517d
Source dataset
uspto-grants-1990_12
Patent number
US04980287

Reaction notes

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