4,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one → 4,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 238458Notes

Reaction equation

HRID 238458 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[C:5](=O)[NH:4][CH2:3]1>C1COCC1>[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][NH:4][CH2:3]1

Participants

3

Reactant 1

HCID 142099534,4-Dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 219596554,4-Dimethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,4-Dimethyl-7-nitro-3,4-dihydro-2H-isoquinolin-1-one (230 mg) was dissolved in THF (10 ml) and BH3Me2S (400 ul) was added and the reaction was stirred overnight at RT. The reaction was quenched with MeOH (10 ml) and NaOH (200 mg) and heating at reflux for 20 min. The mixture was extracted with EtOAc, washed with sat'd NH4Cl, extracted with 10% HCl (20 ml). The acidic solution was treated with 5N NaOH (15 ml), extracted with EtOAc (30 ml) dried, filtered and evaporated to give the compound as a yellow solid. M+H 207.2, Calc'd 206.

Workup

  1. additionBH3Me2S (400 ul) was added
  2. customThe reaction was quenched with MeOH (10 ml) and NaOH (200 mg)
  3. temperatureheating
  4. temperatureat reflux for 20 min
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with sat'd NH4Cl
  7. extractionextracted with 10% HCl (20 ml)
  8. additionThe acidic solution was treated with 5N NaOH (15 ml)
  9. extractionextracted with EtOAc (30 ml)
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-67a10b7e348248cbb501dc5e6d51a5f0
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

Loading…