Formic Acid → HCID 178508682, compound

HRID 1421487Notes

Reaction equation

HRID 1421487 reaction equation
[NH2:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[C:10]([C:11]#N)[C:5]2=[C:4]([NH2:13])[N:3]=1.C(O)=[O:15]>[Ni]>[NH2:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[C:10]([CH:11]=[O:15])[C:5]2=[C:4]([NH2:13])[N:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 178510333HCID 178510333, compound

Product 1

HCID 178508682HCID 178508682, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
80 °C

Procedure

About 6.0 g of Raney Ni was added to a stirred solution of about 2.0 g of Compound 12 and about 50 ml of HCOOH. The mixture was heated to about 80° C. for about 2 hours, until no starting material could be detected by TLC. The mixture was cooled to room temperature and filtered through Celite®. The filtrate was evaporated under reduced pressure, azeotroping with methanol to remove traces of HCOOH. The residue was dissolved in about 25 ml of hot water, treated with Norit®, an activated adsorption carbon commercially available from American Norit Company, Inc., and filtered through Celite®. The filtrate was neutralized with NH4OH. The light brown precipitate which resulted was filtered and dried to yield about 1.40 g of Compound 13, which was immediately used in subsequent reactions without further purification.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite®
  3. customThe filtrate was evaporated under reduced pressure
  4. customazeotroping with methanol
  5. customto remove traces of HCOOH
  6. dissolutionThe residue was dissolved in about 25 ml of hot water
  7. additiontreated with Norit®
  8. filtration, and filtered through Celite®
  9. customThe light brown precipitate which resulted
  10. filtrationwas filtered
  11. customdried

Sources & evidence

ORD record
ord-0a540f2bb8a2489ab4058c0bc9222a34
Source dataset
uspto-grants-2000_06
Patent number
US06077844

Reaction notes

Loading…