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

HRID 1014307Notes

Reaction equation

HRID 1014307 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bf7b216771ee4550b128e5b18fe775a0
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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