Acetic Acid → Methyl 4-(4-oxo-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

HRID 991010

반응식

HRID 991010 반응식
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[O-:23][Bi](=O)=O.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>CO.O>[O:23]=[C:12]1[C:4]2[C:3]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)=[N:2][NH:1][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4063671Sodium bismuthate2회HCID 18415839HCID 18415839, 화합물

생성물 1

HCID 9796477Methyl 4-(4-oxo-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A mixture of methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate (6.3 g, Example 7), sodium bismuthate (31 g), glacial acetic acid (180 ml) and water (60 ml) was boiled under reflux for about 3.5 hours. A further amount of sodium bismuthate (33 g) was added and the mixture boiled under reflux for about 24 hours, then cooled. The pH of the reaction mixture was adjusted to 8-9 by addition of saturated sodium bicarbonate solution. The reaction mixture was filtered through a celite pad and the residue solid washed with ethyl acetate. The organic layer was separated, dried, filtered and evaporated to give a brown solid. The solid was boiled up in methanol (50 ml), cooled and the solid was filtered off, then dried to give methyl 4-(4-oxo-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate, m.p. dec. 235° C.

후처리

  1. temperatureunder reflux for about 3.5 hours
  2. temperatureunder reflux for about 24 hours
  3. temperaturecooled
  4. filtrationThe reaction mixture was filtered through a celite pad
  5. washthe residue solid washed with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto give a brown solid
  11. temperaturecooled
  12. filtrationthe solid was filtered off
  13. customdried

출처 및 근거

ORD 기록
ord-4806c8fb898c481f9a233418259f6b1c
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06462036B1

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