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

HRID 1084441노트

반응식

HRID 1084441 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

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%].

후처리

  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

출처 및 근거

ORD 기록
ord-c3df0a03e08c4fa39bee29fdf27af4cd
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004747

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