Acetonitrile → HCID 19955413, compound

HRID 1779337Notes

Reaction equation

HRID 1779337 reaction equation
C([O-])=O.[NH4+].[N+:5]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[C:11]([C:17]([O:19][CH3:20])=[O:18])[NH:12]2)([O-])=O.C(#N)C>[Pd].CO>[NH2:5][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[C:11]([C:17]([O:19][CH3:20])=[O:18])[NH:12]2

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 2723923Ammonium formateHCID 21187573HCID 21187573, compound

Product 1

HCID 19955413HCID 19955413, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (63 g, 1.00 mol) was added cautiously to a suspension of the product of Example 2 (45.6 g, 0.207 mol) and 10% palladium on charcoal (5 g) in methanol (700 ml) under an argon blanket at 45° C. The mixture was stirred for 4 h, cooled to room temperature, and after 18 h filtered and evaporated in vacuo to give a dark brown semi-solid. This was taken up into acetonitrile (500 ml), filtered (to remove ammonium formate) and evaporated in vacuo to give a dark brown gum. Purification by column chromatography [silica; ethyl acetate-hexane (1:10 to 1:1)] gave the product (9.5 g) as a grey solid.

Workup

  1. filtrationafter 18 h filtered
  2. customevaporated in vacuo
  3. customto give a dark brown semi-solid
  4. filtrationfiltered
  5. custom(to remove ammonium formate)
  6. customevaporated in vacuo
  7. customto give a dark brown gum
  8. customPurification by column chromatography [silica; ethyl acetate-hexane (1:10 to 1:1)]

Sources & evidence

ORD record
ord-ac0c8851727d4ea5a25d045d081f1023
Source dataset
uspto-grants-1997_05
Patent number
US05627177

Reaction notes

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