4-Methylphenylhydrazine monohydrochloride → 3-(1-(Benzyloxy)-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-amine

HRID 2069118ノート

反応式

HRID 2069118 の反応式
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[CH2:11]([O:18][CH2:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CCO>[CH2:11]([O:18][CH2:19][C:20]([C:21]1[CH:22]=[C:23]([NH2:24])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:10])=[CH:3][CH:4]=2)[N:9]=1)([CH3:26])[CH3:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 516892Sodium BicarbonateHCID 585647415-(Benzyloxy)-4,4-dimethyl-3-oxopentanenitrile

生成物 1

HCID 674237623-(1-(Benzyloxy)-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-amine収率 62%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of p-tolylhydrazine hydrochloride (1.99 g, 12.6 mmol) and 5-(benzyloxy)-4,4-dimethyl-3-oxopentanenitrile (4.00 g, 13.8 mmol, 80% purity) in EtOH was heated at reflux for 16 hr and then cooled to RT. The mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 80 g, MeOH in DCM, 0-5%, gradient elution) to afford the title compound, (2.62 g, 60%); Rt 3.05 min (Method 1 basic); m/z 336 (M+H)+ (ES+).

後処理

  1. temperatureat reflux for 16 hr
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 80 g, MeOH in DCM, 0-5%, gradient elution)

出典と根拠

ORDレコード
ord-c641257503ad4bb780cb830fed514eca
出典データセット
uspto-grants-2012_10
特許番号
US08299074B2

反応ノート

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