[4-(1,3-Benzoxazol-2-yl)-2-nitrophenyl]acetonitrile → [2-Amino-4-(1,3-benzoxazol-2-yl)phenyl]acetonitrile

HRID 7697Notes

Reaction equation

HRID 7697 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([N+:19]([O-])=O)[CH:11]=1>CCO.CCOC(C)=O.[Pd]>[NH2:19][C:12]1[CH:11]=[C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH:15]=[CH:14][C:13]=1[CH2:16][C:17]#[N:18]

Participants

4

Reactant 1

HCID 10149379[4-(1,3-Benzoxazol-2-yl)-2-nitrophenyl]acetonitrile

Product 1

HCID 10149213[2-Amino-4-(1,3-benzoxazol-2-yl)phenyl]acetonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A suspension of [4-(1,3-benzoxazol-2-yl)-2-nitrophenyl]acetonitrile (100 mg, 0.36 mmol) and Pd/C (20 mg) in EtOH/EtOAc (5:1, 60 mL) was hydrogenated (35 psi) over 2d. The resulting reaction mixture was filtered through Celite and the filtrate was evaporated to dryness. The yellow solid obtained was purified by flash chromatography on silica gel eluting with MeOH:CH2Cl2 (1:19) to afford [2-amino-4-(1,3-benzoxazol-2-yl)phenyl]acetonitrile as an orange solid (M.p. 198–199° C.). 1H NMR (CDCl3, 300 MHz) δ 7.77 (m, 1H), 7.71–7.66 (m, 2H), 7.58 (m, 1H), 7.40–7.34 (m, 3H), 3.88 (s, 2H), 3.66 (s, 2H). MS (ESI) 250 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through Celite
  3. customthe filtrate was evaporated to dryness
  4. customThe yellow solid obtained
  5. customwas purified by flash chromatography on silica gel eluting with MeOH:CH2Cl2 (1:19)

Sources & evidence

ORD record
ord-e7e8b7f610a94a819838d01e0158ca0b
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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