Methanol → 6-Methoxy-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1014307ノート

反応式

HRID 1014307 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:9](=O)[NH:8][CH2:7][CH2:6]2.CO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2

参加物

4

反応物 2

HCID 887MethanolHCID 594417296-Methoxy-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

生成物 1

HCID 594418746-Methoxy-7-nitro-1,2,3,4-tetrahydroisoquinoline収率 84.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-isoquinolinone (7 g, 31.5 mmol) in THF (800 mL) was treated with 2M BH3 in THF(78.8 mL, 157.6 mmol) and heated to reflux for 20 h. Methanol (100 mL) was added and the solution was concentrated under reduced pressure. The resulting residue was heated with 2N HCl for 3 hr., cooled, basified via careful addition of aqueous ammonium hydroxide, and extracted with dichloromethane. The organic layer was dried, filtered, and taken to a residue under reduced pressure to afford 6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (5.5 g crude, 84.5% pure).

後処理

  1. temperatureto reflux for 20 h
  2. concentrationthe solution was concentrated under reduced pressure
  3. temperatureThe resulting residue was heated with 2N HCl for 3 hr
  4. temperature, cooled, basified via careful addition of aqueous ammonium hydroxide
  5. extractionextracted with dichloromethane
  6. customThe organic layer was dried
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-bf7b216771ee4550b128e5b18fe775a0
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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