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

HRID 419879ノート

反応式

HRID 419879 の反応式
[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

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 21770647HCID 21770647、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-face5309d68e4306853ae9f1b61cee07
出典データセット
uspto-grants-2012_01
特許番号
US08093401B2

反応ノート

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