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

HRID 1715854
Notes
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Reaction equation

HRID 1715854 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 25517Ammonium ChlorideHCID 684327391-(5-Chloro-2-methoxy-benzenesulfonyl)-7-nitro-1,2,3,4-tetrahydro-quinoline

Product 1

HCID 684327061-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst
HCID 962
Water
Solvent

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

  1. temperatureThe mixture was warmed to room temperature
  2. filtrationAfter filtering off the solids
  3. customthe organic solvent was evaporated
  4. extractionthe residual slurry extracted several times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customevaporated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes