Phthalic Anhydride → 2-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

HRID 402555

반응식

HRID 402555 반응식
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].NC(N)=[O:23].OO.C1(=O)OC(=O)C2=CC=CC=C12.[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N+:14]=2[O-:23])[CH:10]=[CH:11][CH:12]=1)=[O:20])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 5

HCID 6811Phthalic Anhydride2회HCID 10340Sodium CarbonateHCID 24437Sodium Sulfite2회HCID 31294Carbamide PeroxideHCID 57516851tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

생성물 1

HCID 584883712-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0.3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45° C. After completion of the phthalic anhydride addition, the mixture was heated to 45° C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2SO3 (1.5 eq) was added via addition funnel. After completion of Na2SO3 addition, the mixture was stirred for an additional 30 minutes, and the layers separated. The organic layer was stirred, and 10% wt/wt aqueous. Na2CO3 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that was used directly in the next step.

후처리

  1. temperatureto maintain the temperature in the reactor below 45° C
  2. stirringthe mixture was stirred for an additional 30 minutes
  3. customthe layers separated
  4. stirringThe organic layer was stirred
  5. stirringAfter stirring for 30 minutes
  6. customto separate
  7. washThe organic phase was washed 13%
  8. filtrationThe organic phase was then filtered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c7d12dac8bdc4577808ab3df38b69548
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742122B2

연결된 노트

불러오는 중…