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

HRID 577542ノート

反応式

HRID 577542 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-890cf07215974bcbabfc3c27a03aeb14
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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