Ethyl 2-chloroacetoacetate → 5-Ethyl-2-methyl-nicotinic acid ethyl ester

HRID 1650881

반응식

HRID 1650881 반응식
C([O-])(=O)C.[NH4+:5].[CH2:6]([C:8](=[CH2:11])[CH:9]=O)[CH3:7].Cl[CH:13]([C:19]([CH3:21])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)(=O)C>[CH2:6]([C:8]1[CH:9]=[N:5][C:19]([CH3:21])=[C:13]([CH:11]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:7]

참가 물질

5

반응물 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 70203EthylacroleinHCID 517165Ammonium Acetate

생성물 1

HCID 144366265-Ethyl-2-methyl-nicotinic acid ethyl ester수율 60.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A suspension of 2 kg of ammonium acetate (26 moles) in 4.5 L of acetic acid is mechanically stirred in a 12 L 4-necked flask equipped with a condenser, and treated with 1 kg of 2-ethylacrolein (11.9 moles) in a single portion followed by 2 kg of ethyl 2-chloroacetoacetate (12.1 moles). An exotherm ensues over a period of 5 minutes to the boiling point of the solvent; this condition is maintained (under control) with air cooling for 10 minutes. After stirring overnight at ambient temperatures, the reaction mixture is filtered, the filtrate is concentrated in vacuo, and the residue is partitioned between 2:1 hexane-ethyl acetate and water. The organic phase is washed with water, then extracted thoroughly with 5% aqueous HCl. The combined aqueous extracts are washed with 2:1 hexane-ethyl acetate, made basic with concentrated NH2OH, and extracted with 2:1 hexane-ethyl acetate. The combined organic extracts are dried and concentrated in vacuo, to give an oil residue which is vacuum distilled to afford 1.4 kg of the title product, bp 90°/0.05 mm.

후처리

  1. customequipped with a condenser
  2. temperaturethis condition is maintained (under control) with air
  3. temperaturecooling for 10 minutes
  4. stirringAfter stirring overnight at ambient temperatures
  5. filtrationthe reaction mixture is filtered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customthe residue is partitioned between 2:1 hexane-ethyl acetate and water
  8. washThe organic phase is washed with water
  9. extractionextracted thoroughly with 5% aqueous HCl
  10. washThe combined aqueous extracts are washed with 2:1 hexane-ethyl acetate
  11. extractionextracted with 2:1 hexane-ethyl acetate
  12. customThe combined organic extracts are dried
  13. concentrationconcentrated in vacuo
  14. customto give an oil residue which
  15. distillationdistilled

출처 및 근거

ORD 기록
ord-dd2bbd0305914c338e5b926e249c9c1d
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04925944

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