HCID 18629909, compound → HCID 18629911, compound

HRID 1059483Notes

Reaction equation

HRID 1059483 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([CH2:13][C:14]#[N:15])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>[Pd].C1COCC1.C(O)(=O)C>[NH2:1][C:4]1[C:9]2[N:10]=[C:11]([CH2:13][C:14]#[N:15])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 18629909HCID 18629909, compound

Product 1

HCID 18629911HCID 18629911, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 4-nitro-2-benzoxazoleacetonitrile (27.22 g, 0.13 mole) and Palladium on carbon (3 g) in THF (320 ml) and acetic acid (5 ml) in a Parr bottle was hydrogenated at 50 psi for 15 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 triturated with isopropyl ether and propyl acetate and filtered to give 4-amino-2-benzoxazoleacetonitrile (14.16 g, 61%).

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 triturated with isopropyl ether and propyl acetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-f9109207cca944d6ba22065406ded143
Source dataset
uspto-grants-2003_02
Patent number
US06521397B1

Reaction notes

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