2-(Azidomethyl)-1,3-benzoxazole → 1-(1,3-Benzoxazol-2-yl)methanamine

HRID 1378722Notes

Reaction equation

HRID 1378722 reaction equation
[N:1]([CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

4

Reactant 1

HCID 229128932-(Azidomethyl)-1,3-benzoxazole

Product 1

HCID 14155281-(1,3-Benzoxazol-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8.28 g (47.5 mmol) of 2-(azidomethyl)benzoxazole (PREPARATION 5) and 0.526 g of 10% Palladium on charcoal in absolute ethanol (150 ml) is shaken under hydrogen at 36 psi for 40 min. The catalyst is then filtered off and the filtrate is concentrated. The crude product is chromatographed on silica gel (700 ml) eluting with methanol/dichloromethane (2/98), the appropriate fractions are pooled and concentrated to give the product. Crystallization from ethyl ether/hexane gives the title compound, mp 46.5°-47.5°; MS (m/z) at 148; NMR (CDCl3) 1.70, 4.14, 7.33, 7.51, 7.70 δ.

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe crude product is chromatographed on silica gel (700 ml)
  4. washeluting with methanol/dichloromethane (2/98)
  5. concentrationconcentrated
  6. customto give the product
  7. customCrystallization from ethyl ether/hexane

Sources & evidence

ORD record
ord-d7ef5936b9c54e1ebc9928d290ad8cd4
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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