Ammonium formate → HCID 66736111, compound

HRID 1640966Notes

Reaction equation

HRID 1640966 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([N+:19]([O-])=O)=[C:14]([CH:18]=2)[C:15]([NH2:17])=[O:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:19][C:13]1[CH:12]=[CH:11][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:18][C:14]=1[C:15]([NH2:17])=[O:16]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 66735912HCID 66735912, compound

Product 1

HCID 66736111HCID 66736111, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-Benzenesulfonyl-2-nitro-benzamide (3.13 g, 10.23 mmol) was suspended in absolute ethanol (200 mL), treated with 10% Pd/C (1.5 g) and then with ammonium formate (9.7 g, 153 mmol). The mixture was stirred at reflux. After a couple of hours the reaction was complete. After cooling to room temperature the reaction was filtered over celite and the panel was washed with EtOH. Evaporation of the filtrate left the crude product that was taken up with a small amount of methanol and added dropwise to 400 mL of iced water kept under stirring. The solid thus formed was filtered and washed with water affording 1.87 g of title compound (66% yield).

Workup

  1. temperatureat reflux
  2. waitAfter a couple of hours the reaction was complete
  3. filtrationwas filtered over celite
  4. washthe panel was washed with EtOH
  5. customEvaporation of the filtrate
  6. waitleft the crude product that
  7. additionadded dropwise to 400 mL of iced water
  8. stirringunder stirring
  9. customThe solid thus formed
  10. filtrationwas filtered

Sources & evidence

ORD record
ord-1a8d5d4fe56146ceb40e1183caa9035b
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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