Iodine → 7-Nitroisoquinoline

HRID 2362264Notes

Reaction equation

HRID 2362264 reaction equation
II.[N+:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][CH2:13]2)=[CH:8][CH:7]=1)([O-:5])=[O:4]>C(O)C>[N+:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[CH:13]2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 807IodineHCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinoline

Product 1

HCID 122162777-NitroisoquinolineYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under refluxing, a solution of iodine (4.0 g, 15.9 mmol) in ethanol (56 mL) was added dropwise to a stirred solution of 31-2 (2.0 g, 9.34 mmol) in ethanol (24 mL) during 5 h. Then the resulted mixture was stirred for a further 66 h. The solvent was removed and the residual was loaded onto a silica gel chromatography column (PE:EA=6:1) to give 31-3 as a brown dark solid (602 mg, yield 36%).

Workup

  1. temperatureUnder refluxing
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-0431b1f298684fcdb96b4568ccbafa76
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

Loading…