Ammonium Chloride → Ethyl 1-(4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 2195541

반응식

HRID 2195541 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11](=[C:17]([CH3:19])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:4][CH:3]=1.[CH3:20]OC(OC)N(C)C.[NH4+].[Cl-]>CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:20]=[CH:19][C:17]([CH3:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 78373Dimethylformamide dimethyl acetalHCID 66767015Ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoate

생성물 1

HCID 66767143Ethyl 1-(4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate수율 62.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

A mixture of ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoate (1.85 g, 6.97 mmol) and N,N-dimethylformamide dimethyl acetal (5 mL, 37.45 mmol) is stirred at 90° C. for 90 min. After the reaction is cooled, EtOAc (30 mL) and saturated NH4Cl solution (20 mL) are added. The organic phase is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (10:1). The fractions containing product are concentrated, and the residue is mixed with ether to give 1.2 g of yellow solid which is filtered and discarded. The filtrate is concentrated and purified again by silica gel column chromatography eluting with DCM:MeOH (20:1) to give the product (500 mg, 26% yield). MS (m/z): 276.1 (M+H).

후처리

  1. temperatureAfter the reaction is cooled
  2. customThe organic phase is separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with DCM:MeOH (10:1)
  7. additionThe fractions containing product
  8. concentrationare concentrated
  9. additionthe residue is mixed with ether

출처 및 근거

ORD 기록
ord-0aa1cb2fe09842b09a49d36bdbea97aa
출처 데이터셋
uspto-grants-2012_12
특허 번호
USRE043878E1

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