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

HRID 1613580ノート

反応式

HRID 1613580 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8000de175e104c289ef133571b5e0bad
出典データセット
uspto-grants-1993_03
特許番号
US05194439

反応ノート

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