Formic Acid → HCID 66738305, compound

HRID 1640917Notes

Reaction equation

HRID 1640917 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:5])=[N+]=[N-].C(O)=O.NN>[Ni].C(O)C>[S:18]1[CH:19]=[CH:20][C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:11]3[CH:10]=[CH:9][N:8]=[CH:7][C:6]=3[CH:4]([NH2:1])[CH3:5])[C:17]1=2

Participants

6

Reactant 3

HCID 284Formic AcidHCID 9321HydrazineHCID 86641876HCID 86641876, compound

Product 1

HCID 66738305HCID 66738305, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Add Raney Nickel (1.38 g, 2.35 mmol) into a solution of 3-(1-azido-ethyl)-4-benzo[b]thiophen-7-yl-pyridine (0.66 g, 2.35 mmol) in ethanol (10 mL), formic acid (1.08 g, 23.54 mmol), and hydrazine (754.4 mg, 23.54 mmol) in a 50-mL round bottom flask in an ice bath. Stir the mixture at RT for 1 h and filter the Raney Nickel. Dilute the filtrate with ammonium hydroxide. Extract the product into chloroform. Wash the organic phase with water, dry over sodium sulfate, and concentrate to give the title compound as a brown oil (0.6 g, 100%). MS (ES) m/z 255 [M+1]+.

Workup

  1. filtrationfilter the Raney Nickel
  2. additionDilute the filtrate with ammonium hydroxide
  3. extractionExtract the product into chloroform
  4. washWash the organic phase with water
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-4568129e40374d878fc2a927a7757156
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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