Acetic Anhydride → 5,6,7,8-Tetrahydro-8-hydroxy-4-methylquinoline

HRID 1613580노트

반응식

HRID 1613580 반응식
[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N+:5]([O-])=[CH:4][CH:3]=1.C(OC(=O)C)(=[O:15])C>>[OH:15][CH:7]1[C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]=2[CH2:10][CH2:9][CH2:8]1

참가 물질

3

반응물 2

HCID 7918Acetic AnhydrideHCID 148359455,6,7,8-tetrahydro 4-methylquinoline-N-oxide

생성물 1

HCID 148359465,6,7,8-Tetrahydro-8-hydroxy-4-methylquinoline

실험 절차

A solution of the crude product of Step 1 (19.2 g, 115 mmol) in acetic anhydride (100 ml) was heated at 110° for 1 h, cooled to room temperature, and evaporated in vacuo. The residue was dissolved in methanol (100 ml) and the solution treated with 4N-NaOH (100 ml). After 2 h, the solution was concentrated in vacuo and the aqueous residue partitioned between dichloromethane (100 ml) and water (100 ml). The chlorinated phase was dried (Na2SO4), and evaporated in vacuo to give an oil which was purified by chromatography (silica; ether) to give the product as crystals (12.0 g).

후처리

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in methanol (100 ml)
  3. additionthe solution treated with 4N-NaOH (100 ml)
  4. concentrationthe solution was concentrated in vacuo
  5. customthe aqueous residue partitioned between dichloromethane (100 ml) and water (100 ml)
  6. dry with materialThe chlorinated phase was dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give an oil which
  9. customwas purified by chromatography (silica; ether)

출처 및 근거

ORD 기록
ord-8000de175e104c289ef133571b5e0bad
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05194439

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