Hydrochloric Acid → HCID 20150296, compound

HRID 568340Notes

Reaction equation

HRID 568340 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:8]=[C:7]2[O:20][CH2:21][C:22]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.C(OCC)C.C(O)(C)C.C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:8]=[C:7]2[O:20][CH2:21][C:22]([N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[O:23]

Participants

10

Reactant 4

HCID 313Hydrochloric Acid3×HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 20150314HCID 20150314, compound

Product 1

HCID 20150296HCID 20150296, compoundYield 10%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4-[(6-Nitro-2-phenyl-4-quinolyl)oxyacetyl]morpholine (12.5 g) in ethanol (550 cc) is heated under reflux for 10 minutes and a solution of sodium dithionite (27.7 g) in water (277 cc) is added in the course of 25 minutes. The mixture is cooled to room temperature (approximately 20° C.) and the ethanol removed under reduced pressure. The aqueous phase is stirred with ethyl acetate and the organic phase is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue obtained is taken up in ethyl ether and converted to the crude hydrochloride by adding a solution of hydrochloric acid in isopropanol. The hydrochloride is taken up with ethyl acetate and aqueous sodium carbonate solution. The precipitate which separates is filtered, heated for 25 minutes in refluxing ethyl acetate, filtered off and dried. 4-[(6-Amino-2-phenyl-4-quinolyl)oxyacetyl]morpholine (1.15 g), m.p. 194° C., is thereby isolated.

Workup

  1. temperatureunder reflux for 10 minutes
  2. customthe ethanol removed under reduced pressure
  3. washthe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue obtained
  7. filtrationThe precipitate which separates is filtered
  8. temperatureheated for 25 minutes
  9. temperaturein refluxing ethyl acetate
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-126ffc3651404930a0e9ed8dc9d1b96d
Source dataset
uspto-grants-1988_03
Patent number
US04728647

Reaction notes

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