HCID 20063346, compound → HCID 86744705, compound

HRID 1084444Notes

Reaction equation

HRID 1084444 reaction equation
[CH3:1][N:2]1[C:11](/[CH:12]=[CH:13]/[CH2:14][OH:15])=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:22]>C(OCC)C.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:11](/[CH:12]=[CH:13]/[CH:14]=[O:15])=[C:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:22]

Participants

4

Reactant 1

HCID 20063346HCID 20063346, compound

Product 1

HCID 86744705HCID 86744705, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of (E)-3-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)prop-2-en-1-ol (0.4 g) in dry diethyl ether (125 ml) under an atmosphere of nitrogen was treated with activated manganese dioxide (1.8 g). The mixture was stirred for 4 hours. The manganese dioxide was then filtered off and washed well with diethyl ether (4×100 ml) during 15 minutes. The combined ethereal solutions were evaporated, to give (E)-3-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)propenal (0.34 g) in the form of a yellow solid, m.p. 228° C.

Workup

  1. filtrationThe manganese dioxide was then filtered off
  2. washwashed well with diethyl ether (4×100 ml) during 15 minutes
  3. customThe combined ethereal solutions were evaporated

Sources & evidence

ORD record
ord-dd7b015365484e95b7466f3d2f0b812f
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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