Acetic Acid → 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride

HRID 221866

反応式

HRID 221866 の反応式
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[ClH:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:19][NH2:20])[CH:16]=[CH:17][CH:18]=1.C(O)(=O)C>C(O)C>[ClH:10].[C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH3:11])[CH:14]=2)[N:20]=1)([CH3:9])([CH3:8])[CH3:1]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27239403-Methoxyphenylhydrazine hydrochloride

生成物 1

HCID 670222745-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride収率 56%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 4,4-dimethyl-3-oxo-pentanenitrile (5.0 g, 40 mmol) and 3-methoxy-phenylhydrazine hydrochloride (7.0 g, 40 mmol) in anhydrous ethanol (200 mL) was added acetic acid (1.2 mL). The reaction mixture was heated at reflux overnight, then cooled to room temperature and concentrated at reduced pressure. The residue was combined with ethyl acetate (200 mL), and washed with saturated aq NaHCO3, water, and brine. The solution was dried over Na2SO4, evaporated at reduced pressure and the solid residue was re-dissolved in ethanol (100 mL). A solution of 2M HCl in ether was added and the mixture was stirred for 30 min. The solvent was removed at reduced pressure, the solid residue was triturated and washed with hexane (50 mL) and then dried in a vacuum oven overnight to give the product 5-tert-butyl-2-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine hydrochloride (5.46 g, 56%) as an off-white solid. 1H-NMR (DMSO-d6) δ 7.50 (t, 1H), 7.10 (m, 3H), 5.60 (s, 1H), 3.80 (s, 3H), 1.30 (s, 9H); MS LC-MS [M+H]+=246.2, RT=1.90 min.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated at reduced pressure
  4. washwashed with saturated aq NaHCO3, water, and brine
  5. dry with materialThe solution was dried over Na2SO4
  6. customevaporated at reduced pressure
  7. dissolutionthe solid residue was re-dissolved in ethanol (100 mL)
  8. additionA solution of 2M HCl in ether was added
  9. customThe solvent was removed at reduced pressure
  10. customthe solid residue was triturated
  11. washwashed with hexane (50 mL)
  12. customdried in a vacuum oven overnight

出典と根拠

ORDレコード
ord-51567a5ef0f44559aad74e4541740fbb
出典データセット
uspto-grants-2012_06
特許番号
US08207166B2

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