Nitric Acid → 4-nitro-5-(propan-2-yl)-1H-pyrazole-3-carboxylic acid

HRID 1063792노트

반응식

HRID 1063792 반응식
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)([CH3:3])[CH3:2].S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[C:5]=1[N+:17]([O-:19])=[O:18])([CH3:3])[CH3:2]

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 7764215-(propan-2-yl)-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 121506014-nitro-5-(propan-2-yl)-1H-pyrazole-3-carboxylic acid수율 80.3%

반응 조건

온도
60 °C

실험 절차

5-Isopropyl-1H-pyrazol-3-carboxylic acid (5 g, 32.5 mmol) was added portionwise to concentrated sulfuric acid (25 ml) at room temperature with stirring. The reaction mixture was then heated to 60° C. and concentrated nitric acid (70%, 6 ml, 90 mmol) was added dropwise, keeping the temperature at 60° C. The reaction was then stirred at 60° C. for 3 hours, cooled to room temperature and poured onto 50 ml of ice with stirring. After 15 minutes the white precipitate was isolated by filtration, washed with water and dried under reduced pressure to give 5-isopropyl-4-nitro-1H-pyrazol-3-carboxylic acid (5.2 g) as a white solid. 1H NMR (400 MHz, DMSO-D6): δ=13.86-13.93 (1H, brs), 13.50-13.80 (1H, brs), 3.39-3.52 (1H, m), 1.18-1.30 (6H, d) ppm. LRMS (electrospray): m/z [M−H]+ 198.

후처리

  1. customat 60° C
  2. stirringThe reaction was then stirred at 60° C. for 3 hours
  3. temperaturecooled to room temperature
  4. stirringwith stirring
  5. customAfter 15 minutes the white precipitate was isolated by filtration
  6. washwashed with water
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-0f8413c04c944c1e9447926c38529d50
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967204B2

반응 노트

불러오는 중…