Sulfuric Acid → 2-Ethylpyrazolo[1,5-a]pyridine

HRID 408800

반응식

HRID 408800 반응식
[CH2:1]([C:3]1[C:11](C(O)=O)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].S(=O)(=O)(O)O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[CH2:1]([C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 583793202-Ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid

생성물 1

HCID 161162612-Ethylpyrazolo[1,5-a]pyridine수율 82%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

2-Ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (4.1 g, 22 mmol) was stirred in water (100 mL) and sulfuric acid (2.5 mL) was added. The mixture was heated at 70° C. for 2 h and cooled to 20° C. The mixture was poured into ethyl acetate and neutralized with saturated sodium bicarbonate. The extracts were separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were dried (sodium sulfate) and evaporated to give the desired compound (2.6 g, 82%). LCMS for C9H11N2 (M+H)+: m/z=147.1. 1H NMR (300 MHz, DMSO-d6): δ 8.52 (m, 1H), 7.57 (m, 1H), 7.11 (m, 1H), 6.75 (m, 1H), 6.38 (s, 1H), 2.73 (m, 2H), 1.22 (m, 3H).

후처리

  1. temperaturecooled to 20° C
  2. customThe extracts were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (sodium sulfate)
  5. customevaporated

출처 및 근거

ORD 기록
ord-dff0416bf98646839691f01d002b0f15
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759359B2

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