Chloroform → HCID 22401308, compound

HRID 260453Notes

Reaction equation

HRID 260453 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH3:22])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([CH3:19])=[C:8]([CH3:20])[CH:7]=2.C(N(CC)CC)C.C(Cl)(Cl)Cl>CS(C)=O>[CH3:22][N:4]1[C:3]([CH:2]=[O:1])=[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:11]2[C:6](=[CH:7][C:8]([CH3:20])=[C:9]([CH3:19])[CH:10]=2)[C:5]1=[O:21]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8471TriethylamineHCID 10447106HCID 10447106, compound

Product 1

HCID 22401308HCID 22401308, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution 1,2-dihydro-3-hydroxymethyl-2,6,7-trimethyl-1-oxo-4-phenylisoquinoline(Reference Example 1) (1.44 g) in DMSO (30 ml) were added triethylamine (2.25 ml) and sulfur trioxide pyridine complex (2.5 g). The mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added chloroform, which was washed with 2N-HCl and water, followed by drying (MgSO4). The solvent was distilled off to leave 1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenyl-3-isoquinolinecarboaldehyde as colorless crystals (1.03 g).

Workup

  1. washwas washed with 2N-HCl and water
  2. dry with materialby drying (MgSO4)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9527a9b246544ba29d7fc996d74c8d05
Source dataset
uspto-grants-1996_06
Patent number
US05527811

Reaction notes

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