1,2,3,4-Tetrahydro-7-nitroisoquinoline → Isoquinolin-7-amine

HRID 1786382Notes

Reaction equation

HRID 1786382 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>C(O)COCCO.CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinoline

Product 1

HCID 14660277Isoquinolin-7-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8117Diethylene GlycolSolvent

Procedure

A mixture of 7-nitro-1,2,3,4-tetrahydro-isoquinoline (1.5 g, 8.38 mmole) and 10% Pd/C (300 mg) in diethylene glycol (5 mL) was reacted in a Smith Synthesizer under microwave radiation at 220° C. for 25 min. The resulting mixture was diluted with MeOH and filtered. The filtrate was concentrated and diluted with CH2Cl2, washed with sat. aq. NH4Cl and dried over Na2SO4. After filtration and concentration, the title compound was isolated through flash chromatography (eluted with CH2Cl2:MeOH 9:1) as an orange solid. MS: (ES+) 145(M+H). Calc'd. for C9H8N2—144.07.

Workup

  1. customwas reacted in a Smith Synthesizer under microwave radiation at 220° C. for 25 min
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with CH2Cl2
  5. washwashed with sat. aq. NH4Cl
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-0d70fa6020004eb6abce4547e2535631
Source dataset
uspto-grants-2009_03
Patent number
US07507748B2

Reaction notes

Loading…