Ethanol → HCID 70607702, compound

HRID 1863106Notes

Reaction equation

HRID 1863106 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([NH:20][CH:21]([CH3:36])[CH2:22][CH2:23][CH2:24][N:25]4[C:29](=[O:30])[C:28]5=CC=CC=[C:27]5[C:26]4=[O:35])[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH2:39].NN.C(O)C.[OH-:45].[K+]>CCOCC>[C:29]([OH:30])(=[O:45])/[CH:28]=[CH:27]\[C:26]([OH:35])=[O:39].[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([NH:20][CH:21]([CH3:36])[CH2:22][CH2:23][CH2:24][NH2:25])[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12373041HCID 12373041, compound

Product 1

HCID 70607702HCID 70607702, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.5 g (0.014 mole) 2-(4-chlorobenzyloxy)-6-methoxy-8-(4-phthalimido-1-methylbutylamino)quinoline (crude), 6.0 ml 85% hydrazine hydrate, and 100 ml 95% ethanol was refluxed 3 hr. After standing overnight, the mixture was stirred with ether and 20 g 50% aq. KOH. The ether layer was washed with water and sat'd. brine. The aqueous portions were extracted with ether and the washing process repeated. A sat'd solution of 2.0 g maleic acid in methanol was added to the dried (MgSO4) ether solution. There was obtained 5.10 g (71%) of an off-white solid, mp 173°-177°. Recrystallization of the crude maleate from 120 ml 95% ethanol (charcoal) afforded 3.55 g, mp 174°-178°. Further recrystallization from ethanol gave the analytical sample, mp 176°-177.5°.

Workup

  1. temperaturewas refluxed 3 hr
  2. washThe ether layer was washed with water
  3. extractionThe aqueous portions were extracted with ether
  4. additionA sat'd solution of 2.0 g maleic acid in methanol was added to the
  5. dry with materialdried (MgSO4) ether solution

Sources & evidence

ORD record
ord-f716788cff9741128324d58c6b5f5109
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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