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

HRID 218476

반응식

HRID 218476 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb2ef7ff04d641a5ba61d78b182bda24
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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