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

HRID 872162ノート

反応式

HRID 872162 の反応式
[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

参加物

3

反応物 1

HCID 9989818Methyl 2-cyano-4-fluorobenzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-076577aebd0c44ff994bdc18bdb03ff5
出典データセット
uspto-grants-2015_03
特許番号
US08975260B2

反応ノート

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