4,4-Dimethoxy-2-butanone → 2-Methoxy4-(3-methyl-pyrazol-1-yl)-benzoic acid, methyl ester

HRID 1635881노트

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HRID 1635881 반응식
Cl.[NH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:14][CH3:15])[CH:5]=1)[NH2:3].CO[CH:18](OC)[CH2:19][C:20](=O)[CH3:21]>Cl.O.CO>[CH3:15][O:14][C:6]1[CH:5]=[C:4]([N:2]2[CH:18]=[CH:19][C:20]([CH3:21])=[N:3]2)[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

참가 물질

5

반응물 2

HCID 2285484,4-Dimethoxy-2-butanoneHCID 57437908Methyl 4-hydrazinyl-2-methoxybenzoate hydrochloride

생성물 1

HCID 544211052-Methoxy4-(3-methyl-pyrazol-1-yl)-benzoic acid, methyl ester수율 53.7%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
90 °C

실험 절차

To a stirred solution of 4-hydrazino-2-methoxybenzoic acid, methyl ester hydrochloride (0.88 g) from Example 104 and one drop of concentrated hydrochloric acid in a 1:1 water/methanol (10 ml) mixture was added acetylacetaldehyde dimethylacetal (0.53 g). The reaction was heated to 90° C. for 5 minutes. The reaction was concentrated in vacuo and partitioned between 1 N sodium hydroxide (10 ml) and ethyl acetate (50 ml). The organic phase was removed and washed with brine, dried over anhydrous magnesium sulfate and filtered. Evaporation of the solvent in vacuo afforded a brown oil which was combined with a previous lot (0.54 g) and recrystallized three times from diisopropyl ether to give 2-methoxy4-(3-methyl-pyrazol-1-yl)-benzoic acid, methyl ester (0.5 g). m.p. 167-169° C., MS, m/z: 246 (M)+.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between 1 N sodium hydroxide (10 ml) and ethyl acetate (50 ml)
  3. customThe organic phase was removed
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customEvaporation of the solvent in vacuo
  8. customafforded a brown oil which
  9. customrecrystallized three times from diisopropyl ether

출처 및 근거

ORD 기록
ord-978f1c40182e4cf0ba5da54f1b323950
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06511974B1

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