1-(3-Fluorophenyl)-3,4-dihydroisoquinoline → 1-(3-Fluorophenyl)isoquinoline

HRID 84133

Reaction equation

HRID 84133 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1>ClC1C=CC=CC=1Cl.[Mn]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 149989031-(3-Fluorophenyl)-3,4-dihydroisoquinoline

Product 1

HCID 111836691-(3-Fluorophenyl)isoquinolineYield 100.2%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
165 °C

Procedure

266.41 g (1.183 mol) of 1-(3-fluorophenyl)-3,4-dihydroisoquinoline were dissolved in 1500 ml of o-dichlorobenzene and admixed with 901.2 g (10.37 mol, 8.7 eq.) of manganese. The mixture was stirred at 160-170° C. for 16 h. Subsequently, the reaction solution was filtered through Celite which was rinsed with dichloromethane/ethanol (25:1). Subsequently, the solvent was distilled off under reduced pressure. 264.74 g of a crystalline solid with 99% purity were obtained, corresponding to 99% of theory.

Workup

  1. filtrationSubsequently, the reaction solution was filtered through Celite which
  2. washwas rinsed with dichloromethane/ethanol (25:1)
  3. distillationSubsequently, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-074b9979916f4467bfc2ab558275b767
Source dataset
uspto-grants-2014_09
Patent number
US08846920B2

Linked notes

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