1,2-Dimethoxyethane → 1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine

HRID 1715854Notes

Reaction equation

[Cl-].[NH4+].COCCOC.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH3:33])=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([N+:29]([O-])=O)[CH:27]=3)[CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:15]=1>O.[Zn]>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH3:33])=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([NH2:29])[CH:27]=3)[CH2:22][CH2:21][CH2:20]2)(=[O:17])=[O:18])[CH:15]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A 27% solution of ammonium chloride in water (35.00 mL) was mixed with 1,2-dimethoxyethane (21.00 mL) and the mixture cooled to 15° C. 1-(5-Chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline (1.00 g, 26.10 mmol) was added under vigorous stirring, followed by zinc powder (2.22 g, 33.96 mmol). The mixture was warmed to room temperature and stirred for 1 hour. After filtering off the solids, the organic solvent was evaporated and the residual slurry extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (dichloromethane/methanol gradient) to yield 1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine as a brown solid, 0.32 g (35%), MS (ISP): m/e=353.2 (M+H).

Workup

temperatureThe mixture was warmed to room temperature
filtrationAfter filtering off the solids
customthe organic solvent was evaporated
extractionthe residual slurry extracted several times with ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulphate
customevaporated
customThe residue was purified by flash chromatography (dichloromethane/methanol gradient)

Sources & evidence

ORD record: ord-6fc785cbefbf444faa25ebdda12db092
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799933B2

Reaction notes

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