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

HRID 1084441ノート

反応式

HRID 1084441 の反応式
[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]

参加物

5

反応物 2

HCID 152141953-Hydroxymethyl-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolineHCID 178418287HCID 178418287、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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%].

後処理

  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

出典と根拠

ORDレコード
ord-c3df0a03e08c4fa39bee29fdf27af4cd
出典データセット
uspto-grants-1991_04
特許番号
US05004747

反応ノート

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