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

HRID 1063792ノート

反応式

HRID 1063792 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f8413c04c944c1e9447926c38529d50
出典データセット
uspto-grants-2005_11
特許番号
US06967204B2

反応ノート

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