Ammonium formate → HCID 22626836, compound

HRID 277916Notes

Reaction equation

HRID 277916 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]([N+:12]([O-])=O)C)[CH:4]=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][NH2:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22626818HCID 22626818, compound

Product 1

HCID 22626836HCID 22626836, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-methoxy-3-(1-phenyl-2-nitro-propyl)-benzene (7.8 g, 30.33 mmoles), obtained as described in example 41, ammonium formate (9.56 g, 151.6 mmoles), methanol (80 ml), 10% Pd/C (1.8 g) and 3A molecular sieves (15 g) was kept under reflux for 2 hours, then filtered over celite by washing with methanol and brought to dryness. The residue was taken up with ethyl ether and extracted with 10% HCl. The aqueous phase was basified with K2CO3 and re-extracted with ethyl ether. The organic phase was anhydrified and brought to dryness to give 5.4 g of the title compound (yield: 78.4%).

Workup

  1. customobtained
  2. temperatureunder reflux for 2 hours
  3. filtrationfiltered over celite
  4. washby washing with methanol
  5. extractionextracted with 10% HCl
  6. extractionre-extracted with ethyl ether

Sources & evidence

ORD record
ord-c104bfd7364144e4a6fc627ed6000bc2
Source dataset
uspto-grants-2002_03
Patent number
US06358973B1

Reaction notes

Loading…