3-(Trifluoromethyl)benzoylacetonitrile → alpha-(Hydroxyimino)-beta-oxo-3-(trifluoromethyl)benzenepropanenitrile

HRID 1106697

반응식

HRID 1106697 반응식
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[CH2:3][C:4]#[N:5].[N:16]([O-])=[O:17].[Na+]>C(O)(=O)C.O>[OH:17][N:16]=[C:3]([C:2](=[O:1])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=1)[C:4]#[N:5]

참가 물질

5

반응물 2

HCID 5203043-(Trifluoromethyl)benzoylacetonitrileHCID 23668193Sodium Nitrite

생성물 1

HCID 88254063alpha-(Hydroxyimino)-beta-oxo-3-(trifluoromethyl)benzenepropanenitrile수율 95.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
15 °C

실험 절차

To a solution of 30.0 g of the title compound of Step A in 200 mL of glacial acetic acid was added dropwise a solution of 11.7 g of sodium nitrite in 35 mL of water while maintaining the reaction temperature at about 15° C. with external cooling. Following addition, the external cooling was removed and the suspension was stirred at room temperature overnight and then poured into excess water (about 400 mL). The aqueous suspension was acidified by dropwise addition of concentrated hydrochloric acid (until red to litmus paper) and then extracted with methylene chloride. The organic solution was dried (MgSO4), filtered and concentrated to give 32.5 g of the title compound of Step B as an oil. 1H NMR (CDCl3): δ 8.3 (s,1H), 8.2 (m,1H), 7.9 (m,1H), 7.65 (m,1H); IR (neat) 1670.2 cm-1.

후처리

  1. additionaddition
  2. temperaturethe external cooling
  3. customwas removed
  4. additionpoured into excess water (about 400 mL)
  5. additionThe aqueous suspension was acidified by dropwise addition of concentrated hydrochloric acid (until red to litmus paper)
  6. extractionextracted with methylene chloride
  7. dry with materialThe organic solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-55b0370034864393b89d5cd59fc0a79c
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057352

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