(5,6,7,8-Tetrahydroisoquinolin-3-yl)methanol → 5,6,7,8-Tetrahydroisoquinoline-3-carbaldehyde

HRID 1943159Notes

Reaction equation

HRID 1943159 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([CH2:11][OH:12])[N:2]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([CH:11]=[O:12])[N:2]=1

Participants

4

Reactant 1

HCID 18799805(5,6,7,8-Tetrahydroisoquinolin-3-yl)methanol

Product 1

HCID 187995785,6,7,8-Tetrahydroisoquinoline-3-carbaldehydeYield 77.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-3-isoquinolinylmethanol (572 mg, 3.50 mmol) in (DCM) (10 ml) at rt under argon was treated with manganese dioxide (3.047 g, 35.0 mmol) and then stirred at rt for 2 h. The reaction mixture was then filtered through a thin pad of Kieselguhr, eluting with DCM (50 ml), the organic extracts were evaporated to give the crude product as a brown oil (435 mg, 77%).

Workup

  1. filtrationThe reaction mixture was then filtered through a thin pad of Kieselguhr
  2. washeluting with DCM (50 ml)
  3. customthe organic extracts were evaporated

Sources & evidence

ORD record
ord-b19c5a977e604a02bf151ce9f30ee29f
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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