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

HRID 1014307노트

반응식

HRID 1014307 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bf7b216771ee4550b128e5b18fe775a0
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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