HCID 58008894, compound → HCID 58158302, compound

HRID 217120Notes

Reaction equation

HRID 217120 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:5](=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:13]>C(Cl)Cl.O=[Mn]=O>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[C:5](=[O:14])[N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[C:3]([CH:2]=[O:1])=[CH:12]2

Participants

4

Reactant 1

HCID 58008894HCID 58008894, compound

Product 1

HCID 58158302HCID 58158302, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(hydroxymethyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one 1609 (2.79 g, 10 mmol) in CH2Cl2 (200 mL), MnO2 (5 g) was added and the resulting mixture was stirred at reflux for 3 h. The mixture was allowed to cool to RT, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10-50% EA/PE) to afford the product, 8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinoline-3-carbaldehyde 4101 (2.5 g, 90% yield) as a white solid.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (10-50% EA/PE)

Sources & evidence

ORD record
ord-bf6116556e8b452785f6c9321fe23ee2
Source dataset
uspto-grants-2012_06
Patent number
US08193182B2

Reaction notes

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