HCID 18629908, compound → HCID 18629912, compound

HRID 1059484Notes

Reaction equation

HRID 1059484 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH2:12][C:13]#[N:14])=[N:9][C:8]=2[CH:15]=1)([O-])=O>[Pd].C1COCC1.C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH2:12][C:13]#[N:14])=[N:9][C:8]=2[CH:15]=1

Participants

5

Reactant 1

HCID 18629908HCID 18629908, compound

Product 1

HCID 18629912HCID 18629912, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 5-nitro-2-benzoxazoleacetonitrile (8 g 39.4 mmole) and Palladium on carbon (1.2 g) in THF (100 ml) and acetic acid (2 ml) in a Parr bottle was hydrogenated at 50 psi for 5 h. It was filtered over a patch of celite (1.5 cm) covered with activated carbon (0.5 cm) and washed with isopropyl ether. The filtrate was evaporated and the residue was purified by flash chromatography and gave 5-amino-2-benzoxazoleacetonitrile (2.02 g, 30%).

Workup

  1. filtrationIt was filtered over a patch of celite (1.5 cm)
  2. washwashed with isopropyl ether
  3. customThe filtrate was evaporated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0b95522846a34573b917bf76b588d84b
Source dataset
uspto-grants-2003_02
Patent number
US06521397B1

Reaction notes

Loading…