Nitric Acid → 2-(4-nitro-1H-pyrazol-1-yl)acetic acid

HRID 1686003노트

반응식

HRID 1686003 반응식
C([O:3][C:4](=[O:11])[CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[N:7]1)C.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[N+:17]([C:9]1[CH:8]=[N:7][N:6]([CH2:5][C:4]([OH:3])=[O:11])[CH:10]=1)([O-:19])=[O:18]

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 4534671Ethyl 2-(1H-pyrazol-1-yl)acetate

생성물 1

HCID 12834772-(4-nitro-1H-pyrazol-1-yl)acetic acid수율 33%

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온도
0 °C

실험 절차

Six conical flasks were charged with pyrazol-1-yl-acetic acid ethyl ester (6×9.66 g, 6×62.6 mmol) and concentrated sulphuric acid (6×20 ml) was added. The solutions were cooled to 0° C. and concentrated nitric acid (6×10 ml) was added dropwise. The reaction mixtures were allowed to warm to room temperature and left standing for 18 hours. The combined organic mixtures were poured into ice (50 ml) and extracted with ethyl acetate (5×500 ml). The combined organic extracts were washed with brine (500 ml), dried (MgSO4), filtered and concentrated under reduced pressure to leave a yellow solid. Recrystallisation from ethyl acetate afforded the title compound as an off-white solid (20.97 g, 33% yield).

후처리

  1. additionwas added
  2. customThe reaction mixtures
  3. temperatureto warm to room temperature
  4. waitleft
  5. extractionextracted with ethyl acetate (5×500 ml)
  6. washThe combined organic extracts were washed with brine (500 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto leave a yellow solid
  11. customRecrystallisation from ethyl acetate

출처 및 근거

ORD 기록
ord-c9a8134c836e4947974dd6ff72db73d4
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148531B2

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