3-Hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline → 2-Methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-carbaldehyde

HRID 1084441Notes

Reaction equation

HRID 1084441 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C:14]1[N:15]([CH3:31])[C:16](=[O:30])[C:17]2[C:22]([C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2>ClCCl.C(OCC)C>[CH3:31][N:15]1[C:14]([CH:13]=[O:12])=[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:30]

Participants

5

Reactant 2

HCID 152141953-Hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolineHCID 178418287HCID 178418287, compound

Product 1

HCID 200633422-Methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-carbaldehydeYield 69.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of pyridinium chlorochromate (23.36 g) in dichloromethane (250 ml) was treated with a suspension of 3-hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline (19.1 g) in dichloromethane (1000 ml), and stirred for 1.75 hours. Then the reaction mixture was diluted with diethyl ether (3000 ml), stirred for 20 minutes, and filtered through diatomaceous earth. The filter pad was washed with diethyl ether (1000 ml) and the combined filtrate and washings were filtered through a 3 inch thick pad of silica gel. The filtrate was evaporated and the resulting residue was crystallised from ethyl acetate, to give 2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-carbaldehyde (13.22 g) in the form of white crystals, m.p.181°-182° C. [Elemental analysis: C,77.4; H,4.94; N,5.29%; calculated: C,77.6; H,4.98; N,5.32%].

Workup

  1. stirringstirred for 20 minutes
  2. filtrationfiltered through diatomaceous earth
  3. washThe filter pad was washed with diethyl ether (1000 ml)
  4. filtrationthe combined filtrate and washings were filtered through a 3 inch thick pad of silica gel
  5. customThe filtrate was evaporated
  6. customthe resulting residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-c3df0a03e08c4fa39bee29fdf27af4cd
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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