Methyl 2-cyano-4-fluorobenzoate → 5-fluoro-2,3-dihydro-1H-isoindol-1-one

HRID 872162노트

반응식

HRID 872162 반응식
[C:1]([C:3]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6])#[N:2]>C(O)C>[F:13][C:11]1[CH:12]=[C:3]2[C:4](=[CH:9][CH:10]=1)[C:5](=[O:6])[NH:2][CH2:1]2

참가 물질

3

반응물 1

HCID 9989818Methyl 2-cyano-4-fluorobenzoate

생성물 1

HCID 197880975-fluoro-2,3-dihydro-1H-isoindol-1-one수율 76.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A 250-mL Parr reactor bottle was purged with nitrogen and charged with Raney nickel (4.00 g) and a solution of 106a (2.00 g, 11.2 mmol) in ethanol (20 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 16 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (5.00 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×75 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a 76% yield of 106b (1.29 g) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 7.85 (dd, 1H, J=8.5, 5.5 Hz), 7.21-7.16 (m, 2H), 7.05 (br s, 1H), 4.56 (s, 2H).

후처리

  1. customA 250-mL Parr reactor bottle was purged with nitrogen
  2. additioncharged with Raney nickel (4.00 g)
  3. customevacuated
  4. additioncharged with hydrogen gas to a pressure of 50 psi
  5. customAfter this time, the hydrogen was evacuated
  6. additionnitrogen was charged into the bottle
  7. additionCelite 521 (5.00 g) was added
  8. filtrationthe mixture was filtered through a pad of Celite 521
  9. washThe filter cake was washed with ethanol (2×75 mL)
  10. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-076577aebd0c44ff994bdc18bdb03ff5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975260B2

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