Hydrochloric Acid → N-[2-(4-Methyl-1-oxo-1,2,3,4-tetrahydrobenzo[f]quinolin-10-yl)ethyl]-2-phenylacetamide

HRID 985773Notes

Reaction equation

[CH3:1][N:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([CH2:18][CH2:19][NH:20][C:21](=[O:29])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[CH2:3][CH2:4][C:5](Cl)=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C(Cl)Cl>[CH3:1][N:2]1[C:8]2[CH:17]=[CH:16][C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:18][CH2:19][NH:20][C:21](=[O:29])[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:10]=3[C:9]=2[C:5](=[O:6])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

The product obtained in Step C (3 mmol), dissolved in 1,1,2,2-tetrachloroethane (30 ml), is added dropwise to a solution of aluminium chloride (10 mmol) in the same solvent (20 ml) under nitrogen. The reaction mixture is heated at 60° C., with stirring, until the reaction has ceased and it is then poured into a mixture of ice (10 g) and concentrated HCl (0.3 ml); stirring is continued for one hour. The aqueous phase is extracted twice with chloroform; the combined organic phases are then dried over magnesium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel to yield the title product.

Workup

stirringstirring
extractionThe aqueous phase is extracted twice with chloroform
dry with materialthe combined organic phases are then dried over magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-08614b4c883340598c715004a5259f34
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872851B1

Reaction notes

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