Formic Acid → HCID 53940744, compound

HRID 581916Notes

Reaction equation

HRID 581916 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]4[S:17][CH:18]=[CH:19][N:20]=4)[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#N.C(O)=[O:24]>O.[Ni]>[CH:1]([C:3]1[CH:22]=[CH:21][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]4[S:17][CH:18]=[CH:19][N:20]=4)[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)=[O:24]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 53634835HCID 53634835, compound

Product 1

HCID 53940744HCID 53940744, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Raney Ni (2.0 g) was added to a solution of (54) (1.5 g, 4.9 mmol) in HCO2H (18 ml) and water (6 ml). The mixture was stirred under argon at 110° C. for 1 hr. After cooling the mixture was filtered. The filtrate was concentrated, partitioned between a 5% aqueous NaHCO3 solution and ethyl acetate. The organic phase was washed with brine, dried and concentrated under reduced pressure to give (55) (1.3 g, 87%).

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between a 5% aqueous NaHCO3 solution and ethyl acetate
  5. washThe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87f66a8e95704252b86376d45a3d052e
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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