HCID 26240658, compound → HCID 39423054, compound

HRID 1859751Notes

Reaction equation

HRID 1859751 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N+:20]([O-])=O)[CH:13]=2)[CH:5]=1>[Ni].CN(C)C=O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([NH2:20])[CH:13]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 26240658HCID 26240658, compound

Product 1

HCID 39423054HCID 39423054, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

Raney nickel (1 g) was added to a solution of 3-(3-nitro-4-methoxy-benzoylamino)-benzoic acid methyl ester from Step A (4.0 g, 12 mmol) in dimethylformamide (125 mL) and shaken at room temperature under an atmosphere of hydrogen, initially at a pressure of 50 psi, until the required amount was taken up. The catalyst was removed by filtration and the filtrate was stripped of solvent by rotary evaporator. Recrystallization of the residue from methanol (150 mL) gave the product (2.3 g); m.p. 160-162° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was stripped of solvent by rotary evaporator
  3. customRecrystallization of the residue from methanol (150 mL)

Sources & evidence

ORD record
ord-bdb5a80eb2c343bfa3c1afab9e3bf713
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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