7-Benzyloxy-3-hydroxymethyl-2-methyl-4-(5-methyl-chroman-6-yl)-2H-isoquinolin-1-one → 7-Benzyloxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinoline-3-carbaldehyde

HRID 572491Notes

Reaction equation

HRID 572491 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:23]3[C:24]([CH3:33])=[C:25]4[C:30](=[CH:31][CH:32]=3)[O:29][CH2:28][CH2:27][CH2:26]4)=[C:14]([CH2:21][OH:22])[N:15]([CH3:20])[C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:23]3[C:24]([CH3:33])=[C:25]4[C:30](=[CH:31][CH:32]=3)[O:29][CH2:28][CH2:27][CH2:26]4)=[C:14]([CH:21]=[O:22])[N:15]([CH3:20])[C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 682957767-Benzyloxy-3-hydroxymethyl-2-methyl-4-(5-methyl-chroman-6-yl)-2H-isoquinolin-1-one

Product 1

HCID 867007197-Benzyloxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinoline-3-carbaldehydeYield 86.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-Benzyloxy-3-hydroxymethyl-2-methyl-4-(5-methyl-chroman-6-yl)-2H-isoquinolin-1-one (3.5 g, 7.93 mmol) in dichloromethane (100 ml) was added manganese dioxide (6.89 g, 79.3 mmol). The resultant mixture was stirred at 70° C. under N2 for 2 h. The reaction mixture was filtered and concentrated to dryness to afford the title product (3.0 g, 86%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bdf59b444739425a9a4fc3588e73bb7b
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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