HCID 54113030, compound → HCID 54487936, compound

HRID 482890Notes

Reaction equation

HRID 482890 reaction equation
[CH3:1][C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[CH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[N:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[CH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 54113030HCID 54113030, compound

Product 1

HCID 54487936HCID 54487936, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinemethanol (5.3 g) in chloroform (150 ml) is treated with three portions (4.5 g) of activated manganese dioxide at 4 hour intervals during reflux reaction. The suspension is filtered and the filtrate is evaporated to yield crude 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinecarboxaldehyde (5.3 g) as an oil. Filtration through silica gel (125 g) removes polar products and provides pure 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinecarboxaldehyde (2.1 g). Activated MnO2 (0.45 g) converts 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinemethanol (0.15 g) to 5,6,7,8-tetrahydro-2-methyl-8-methyl(phenylmethylene)-3-quinolinecarboxaldehyde (m.p. 217°-219°) within 15 minutes in toluene (15 ml) under azeotropic distillation conditions.

Workup

  1. temperatureduring reflux
  2. customreaction
  3. filtrationThe suspension is filtered
  4. customthe filtrate is evaporated
  5. customto yield crude 5,6,7,8-tetrahydro-2-methyl-8-(phenylmethylene)-3-quinolinecarboxaldehyde (5.3 g) as an oil
  6. filtrationFiltration through silica gel (125 g)
  7. customremoves polar products

Sources & evidence

ORD record
ord-2c612d7f56ee4723b55a2d796cc49105
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

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