7-Nitro-3,4-dihydroisoquinoline → 7-Nitroisoquinoline

HRID 1953559Notes

Reaction equation

HRID 1953559 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>[Pd].C1C2C(CCCC2)CCC1>[N+: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)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 37512877-Nitro-3,4-dihydroisoquinoline

Product 1

HCID 122162777-NitroisoquinolineYield 55.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7044DecalinSolvent

Procedure

A solution of 7-nitro-3,4-dihydroisoquinoline (3.00 g, 17.0 mmol) and 5% palladium on carbon (3.0 g) in decalin (75 ml) was heated at reflux for 3 h. Upon cooling, the solution was filtered and the catalyst washed with chloroform (200 ml). The solvent was removed in vacuo to give 7-nitroisoquinoline (1.63 g) as a tan solid. MS 175 (M+H).

Workup

  1. temperatureat reflux for 3 h
  2. temperatureUpon cooling
  3. filtrationthe solution was filtered
  4. washthe catalyst washed with chloroform (200 ml)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-75367f544f2b4b9e9a842f5cab05cb4f
Source dataset
uspto-grants-2000_09
Patent number
US06117898

Reaction notes

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