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

HRID 2069118노트

반응식

HRID 2069118 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-c641257503ad4bb780cb830fed514eca
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299074B2

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