Thiophene → 2-Amino-5-benzoylbenzamide

HRID 2247891Notes

Reaction equation

HRID 2247891 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:18]([O-])=O)=[C:13]([CH:17]=1)[C:14]([NH2:16])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC=C1>CO.[Pd]>[NH2:18][C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 198160645-Benzoyl-2-nitrobenzamide

Product 1

HCID 198160482-Amino-5-benzoylbenzamideYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 7.76 parts of intermediate 14, namely 5-benzoyl-2-nitrobenzamide, 2 parts of a solution of thiophene in methanol 4% and 198 parts of methanol was hydrogenated overnight at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. The catalyst was filtered off and washed with tetrahydrofuran. The combined filtrates were evaporated and the residue was co-evaporated with methylbenzene. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH/CH3OH(NH3) 90:5:5). The eluent of the desired fraction was evaporated and the residue was taken up in methanol. This solution was concentrated and the product was filtered off, washed with methanol and 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 2.84 parts (41.0%) of 2-amino-5-benzoylbenzamide; mp. 225.2° C. (interm. 15).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with tetrahydrofuran
  3. customThe combined filtrates were evaporated
  4. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH/CH3OH(NH3) 90:5:5)
  5. customThe eluent of the desired fraction was evaporated
  6. concentrationThis solution was concentrated
  7. filtrationthe product was filtered off
  8. washwashed with methanol and 2,2'-oxybispropane
  9. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-d9949f0069264957b1b8046ab630267c
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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