Hydrazine hydrate (1:1) → 7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

HRID 577542노트

반응식

HRID 577542 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][C:14]1[C:15]([C:24]([O:26]C)=O)=[CH:16][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[N:18][CH:19]=1.O.NN>CCO>[CH3:22][CH:21]([O:20][C:17]1[CH:16]=[C:15]2[C:14]([CH2:13][CH2:12][NH:3][C:24]2=[O:26])=[CH:19][N:18]=1)[CH3:23]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 86723771methyl 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-2-(propan-2-yloxy)pyridine-4-carboxylate

생성물 1

HCID 867237727-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one수율 96%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To methyl 5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-2-(propan-2-yloxy)pyridine-4-carboxylate (112c, 0.630 g, 1.71 mmol) in EtOH (50 mL) was added hydrazine monohydrate (0.850 mL, 17.1 mmol). The reaction mixture was refluxed for 5 hours. The reaction mixture was cooled to room temperature and the white solids collected by filtration and rinsed with EtOH. The mother liquor was concentrated and H2O (25 mL) was added, then the aqueous layer extracted with EtOAc (3×25 mL) The combined organic layers were concentrated under vacuum and purified by column chromatography (0-80% ethyl acetate/heptanes) to give 7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one (112d, 337 mg, 96%) as a white solid.

후처리

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. filtrationthe white solids collected by filtration
  3. washrinsed with EtOH
  4. concentrationThe mother liquor was concentrated
  5. additionH2O (25 mL) was added
  6. extractionthe aqueous layer extracted with EtOAc (3×25 mL) The combined organic layers
  7. concentrationwere concentrated under vacuum
  8. custompurified by column chromatography (0-80% ethyl acetate/heptanes)

출처 및 근거

ORD 기록
ord-890cf07215974bcbabfc3c27a03aeb14
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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