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

HRID 2195541ノート

反応式

HRID 2195541 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0aa1cb2fe09842b09a49d36bdbea97aa
出典データセット
uspto-grants-2012_12
特許番号
USRE043878E1

反応ノート

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