(4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, ethyl ester → 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-2H-1,4-benzoxazin-3(4H)-one

HRID 1735071노트

반응식

HRID 1735071 반응식
[Cl:1][C:2]1[C:3]([C:12]2[C:24]([F:25])=[CH:23][C:15]([O:16][CH2:17][C:18](OCC)=[O:19])=[C:14]([N+:26]([O-])=O)[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:3]([C:12]2[C:24]([F:25])=[CH:23][C:15]3[O:16][CH2:17][C:18](=[O:19])[NH:26][C:14]=3[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]

참가 물질

4

반응물 1

HCID 86747521(4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)acetic acid, ethyl ester

생성물 1

HCID 194367686-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-2H-1,4-benzoxazin-3(4H)-one수율 80%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

A solution of 4.5 g (0.0106 mole) (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)-acetic acid, ethyl ester in 75 mL acetic acid was heated to 80° C. under a nitrogen atmosphere. The heat and nitrogen were removed and 1.8 g (0.033 mole) iron powder was added in 3 portions over 5 min. The solution was stirred at 80° C. for an additional 3 hours. The solution was cooled and filtered through Celite®. The filtrate was diluted with 100 mL water and extracted three times with ethyl acetate. The ethyl acetate extracts were washed with a saturated NaHCO3 solution, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was recrystallized from methylcyclohexane/ethyl acetate to give 2.95 g (80%) of 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-2H-1,4-benzoxazin-3(4H)-one as a white solid, mp 207° C.

후처리

  1. temperatureThe heat
  2. customnitrogen were removed
  3. temperatureThe solution was cooled
  4. filtrationfiltered through Celite®
  5. additionThe filtrate was diluted with 100 mL water
  6. extractionextracted three times with ethyl acetate
  7. washThe ethyl acetate extracts were washed with a saturated NaHCO3 solution
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from methylcyclohexane/ethyl acetate

출처 및 근거

ORD 기록
ord-54b4128028854a25a9b897e5415b5f2e
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05536700

반응 노트

불러오는 중…