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

HRID 1461281노트

반응식

HRID 1461281 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 lh, 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 2h, 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. concentrationAfter 2h, the 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-e34480a463d046248f3f6e3e77e662b7
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075303

반응 노트

불러오는 중…