Hydrochloric Acid → HCID 19833027, compound

HRID 2051178Notes

Reaction equation

HRID 2051178 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18]([O:20][CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:30]([F:33])([F:32])[F:31])[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.Cl.O>CO.C(O)(C)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18]([O:20][CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:30]([F:33])([F:32])[F:31])[N:11]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19833026HCID 19833026, compound

Product 1

HCID 19833027HCID 19833027, compoundYield 51.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

4-{[2-(4-Nitrophenyl)-5-trifluoromethyl-4-quinolyl]oxyacetyl}morpholine (6.6 g) dissolved in methanol (=b 132 cc) is hydrogenated for three hours thirty minutes at atmospheric pressure in the presence of an 8N solution (6.6 cc) of gaseous hydrochloric acid in isopropanol and palladium (0.66 g) supported on charcoal (10% palladium). Distilled water (240 cc) is then added, the mixture is stirred for 10 minutes and the catalyst is thereafter filtered off. Normal aqueous sodium hydroxide solution (45 cc) is added an the precipitate is filtered off, washed with distilled water (3×100 cc) and dried under reduced pressure. The precipitate is dissolved while hot in a cyclohexane/ethyl acetate mixture (50:50 by volume). The solution is filtered and the filtrate is concentrated under reduced pressure. The residue is taken up on petroleum ether, filtered off and dried. 4-{[2-(4-Aminophenyl)-5-trifluoromethyl-4-quinolyl]oxyacetyl}morpholine (3.16 g,), m.p. 174° C., is thereby obtained.

Workup

  1. filtrationthe catalyst is thereafter filtered off
  2. additionNormal aqueous sodium hydroxide solution (45 cc) is added an the precipitate
  3. filtrationis filtered off
  4. washwashed with distilled water (3×100 cc)
  5. customdried under reduced pressure
  6. dissolutionThe precipitate is dissolved while hot in a cyclohexane/ethyl acetate mixture (50:50 by volume)
  7. filtrationThe solution is filtered
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-f16414fa78e14cc197d48f3dc731b0c6
Source dataset
uspto-grants-1991_05
Patent number
US05017576

Reaction notes

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