Water → 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol

HRID 1174839ノート

反応式

HRID 1174839 の反応式
Cl.[C:2]([C:6]1[CH:7]=[C:8]([NH2:19])[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)[N:10]=1)([CH3:5])([CH3:4])[CH3:3].Cl.[NH+]1C=CC=CC=1.O>CCOC(C)=O>[NH2:19][C:8]1[N:9]([C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)[N:10]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 21584435Pyridinium hydrochlorideHCID 670222745-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride

生成物 1

HCID 595579663-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol収率 19%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
195 °C

実験手順

In a 500 mL round bottom flask was added 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride (8.42 g, 30 mmol) and pyridinium hydrochloride (13.8 g, 120 mmol). The reaction mixture was heated neat at 195° C. with stirring for 3 h. The mixture was cooled to room temperature, water (300 mL) and EtOAc (300 mL) were added, and then the organic phase was washed with saturated aq NaHCO3 and brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was purified by MPLC (80:20 hexane/EtOAc) to give the product 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenol (1.3 g, 19%). 1H-NMR (DMSO-d6) δ 7.20 (t, 1H), 7.00 (m, 2H), 6.50 (d, 1H), 5.30 (s, 1H), 5.10 (bs, 2H), 1.30 (s, 9H); MS LC-MS [M+H]+=232.2, RT=0.57 min.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washthe organic phase was washed with saturated aq NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was purified by MPLC (80:20 hexane/EtOAc)

出典と根拠

ORDレコード
ord-0cd0390e4450440fbe469bf0479d133d
出典データセット
uspto-grants-2010_11
特許番号
US07838524B2

反応ノート

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