2-Fluoro-5-formylbenzonitrile → 4-(3-Cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

HRID 218476

反応式

HRID 218476 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][C:3]=1[C:4]#[N:5].[NH2:12]/[C:13](/[CH3:17])=[CH:14]\[C:15]#[N:16]>C(O)(=O)C>[C:4]([C:3]1[CH:6]=[C:7]([CH:10]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[NH:12][C:2]([CH3:9])=[C:3]2[C:4]#[N:5])[CH:8]=[CH:9][C:2]=1[F:1])#[N:5]

参加物

4

反応物 2

HCID 27695822-Fluoro-5-formylbenzonitrileHCID 5325263(2Z)-3-Amino-2-butenenitrile

生成物 1

HCID 597632464-(3-Cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile収率 160.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

2-Fluoro-5-formylbenzonitrile (30 g, 201.17 mmol) and 3-aminocrotononitrile (35.01 g, 431.63 mmol) were dissolved in acetic acid and heated to 90° C. After 4 hr, the reaction mixture was cooled to rt, concentrated, neutralized with a saturated solution of sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate and concentrated. The solid were dissolved into ethyl acetate, and hexane was added. The solid precipitated, and was filtered to afford 4-(3-cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (44.9 g, 80.2%) as a pale yellow solid. 1H-NMR (400 MHZ, DMSO-D6): δ=9.61 (br. s, 1H), 7.97 (dd, 1H), 7.48 (dd, 1H), 7.35 (dd, 1H), 4.64 (s, 1H), 2.01 (s, 6H) ppm.

後処理

  1. temperaturethe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThe solid were dissolved into ethyl acetate, and hexane
  7. additionwas added
  8. customThe solid precipitated
  9. filtrationwas filtered

出典と根拠

ORDレコード
ord-bb2ef7ff04d641a5ba61d78b182bda24
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

関連ノート

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