Hydrochloric Acid → Ethyl 5-(aminomethyl)-2-(difluoromethyl)nicotinate hydrochloride

HRID 241429노트

반응식

HRID 241429 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]([CH:9]([F:11])[F:10])=[N:7][CH:8]=1)#[N:2].[ClH:16].[H][H].[CH3:19]CO>[Pd]>[ClH:16].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:19])=[O:13])[C:6]([CH:9]([F:11])[F:10])=[N:7][CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702Ethanol2회HCID 71059861Methyl 5-cyano-2-(difluoromethyl)pyridine-3-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 71059730Ethyl 5-(aminomethyl)-2-(difluoromethyl)nicotinate hydrochloride수율 96%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

Purge a mixture of methyl 5-cyano-2-(difluoromethyl)pyridine-3-carboxylate (160 g, 707.4 mmol) and EtOH (2 L) with nitrogen and stir 15 min. Add hydrochloric acid (37 wt % aqueous, 273 mL, 3183.2 mmol, 4.5 equiv) and palladium (5% on carbon, 48 g, 22.5 mmol, 0.031 equiv) in EtOH (100 mL), and stir the resulting suspension under 60 psi of hydrogen at room temperature for 70 min. Remove the solids by filtration over diatomaceous earth; wash the solid cake with EtOH (1 L); and concentrate the filtrate under reduced pressure. Repeat this procedure twice; combine the solids; and slurry in Et2O:DCM [10:1, 5.5 L]. Filter the solids and dry the resulting material at 45° C. for 3 hours to give the title compound as a light brown solid (714 g, 96% yield). MS (m/z) 216 (M+1).

후처리

  1. customPurge
  2. customRemove the solids
  3. filtrationby filtration over diatomaceous earth
  4. washwash the solid cake with EtOH (1 L)
  5. concentrationand concentrate the filtrate under reduced pressure
  6. filtrationFilter the solids
  7. customdry the resulting material at 45° C. for 3 hours

출처 및 근거

ORD 기록
ord-48caa241a0a04d9cbcad565a5864bc9b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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