HCID 136042682, compound → HCID 136087745, compound

HRID 235605Notes

Reaction equation

HRID 235605 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:14][N:15]=[C:16]([C:20]1[C:21](=[O:41])[CH2:22][CH:23]([C:27]2[C:36]3[CH2:35][CH2:34][CH2:33][CH:32]([OH:37])[C:31]=3[C:30]([CH3:38])=[N:29][C:28]=2[O:39][CH3:40])[CH2:24][C:25]=1[OH:26])[CH2:17][CH2:18][CH3:19])[CH3:13]>ClCCl>[CH2:12]([O:14][N:15]=[C:16]([C:20]1[C:25](=[O:26])[CH2:24][CH:23]([C:27]2[C:36]3[CH2:35][CH2:34][CH2:33][C:32](=[O:37])[C:31]=3[C:30]([CH3:38])=[N:29][C:28]=2[O:39][CH3:40])[CH2:22][C:21]=1[OH:41])[CH2:17][CH2:18][CH3:19])[CH3:13]

Participants

4

Reactant 2

HCID 136042682HCID 136042682, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 136087745HCID 136087745, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (1.1 equiv) was added in small portions to a stirred solution of 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(8-hydroxy-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)cyclohex-2-en-1-one (0.1 g) in dichloromethane (40 ml) at room temperature. The mixture was filtered through a small silica chromatography column with dichloromethane/ethyl acetate (5:1 v/v) elution to give 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(3-methoxy-1-methyl-8-oxo-5,6,7,8-tetrahydroisoquinolin-4-yl)cyclohex-2-en-1-one as a white solid, mp 162° C. The product was characterized by proton nuclear magnetic resonance spectroscopy and the spectroscopic data is recorded in Table 4, Example 10.

Workup

  1. filtrationThe mixture was filtered through a small silica chromatography column with dichloromethane/ethyl acetate (5:1 v/v) elution

Sources & evidence

ORD record
ord-0c6407e6ba5f490280bdb5f9442045e3
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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