Ammonium Chloride → 3-Oxazolo[4,5-c]pyridin-2-ylbenzenamine

HRID 419879Notes

Reaction equation

HRID 419879 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH4+].[Cl-]>CO.O.[Fe]>[O:11]1[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=[C:10]1[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21770647HCID 21770647, compound

Product 1

HCID 217706513-Oxazolo[4,5-c]pyridin-2-ylbenzenamineYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A suspension of 2-(3-nitrophenyl)oxazolo[4,5-c]pyridine (1.50 g, 6.2 mmol), iron powder (1.867 g, 31.8 mmol) and NH4Cl (2.86 g, 53.5 mmol) in CH3OH/H2O (4: 1, 311.2 mL) was refluxed for 6 h. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel (eluted with petroleum ether: EtOAc : Et3N=160:40:1) to afford 3-(oxazolo[4,5-c]pyridin -2-yl)benzenamine as a white solid (1.107 g, yield: 85%). 1H NMR (400 MHz, DMSO-d6) δ: 5.54 (2H, s), 6.82 (1H, d, J=8.0 Hz), 7.24 (1H, t, J=8.0 Hz), 7.35 (1H, d, J=8.0 Hz), 7.44 (1H, s), 7.86 (1H, d, J=5.6 Hz), 8.56 (1H, d, J=5.6 Hz), 9.07 (1H, s); MS (ESI) calcd. for C12H9N3O (m/z): 211, found: 212 [M+1]+.

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel (eluted with petroleum ether: EtOAc : Et3N=160:40:1)

Sources & evidence

ORD record
ord-face5309d68e4306853ae9f1b61cee07
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

Loading…