Sodium Hydroxide → HCID 555082, compound

HRID 2290654Notes

Reaction equation

HRID 2290654 reaction equation
C([O-])C.[CH3:4][O:5][C:6]1[C:7]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)=[C:8]2[C:13](=[C:14]([N:16]3[C:20](=[O:21])[C:19]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]4[C:17]3=[O:26])[CH:15]=1)[N+:12]([O-])=[CH:11][CH:10]=[C:9]2[CH3:28].O=P(Cl)(Cl)[Cl:42].[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:42][C:11]1[CH:10]=[C:9]([CH3:28])[C:8]2[C:13](=[C:14]([N:16]3[C:17](=[O:26])[C:18]4=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]4[C:20]3=[O:21])[CH:15]=[C:6]([O:5][CH3:4])[C:7]=2[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:37])[F:39])[CH:31]=2)[N:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 70455704HCID 70455704, compound2×

Product 1

HCID 555082HCID 555082, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

From 6-methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline-1-oxide Ethanolate (III): A solution of 6-methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline-1-oxide ethanolate (32.7g, 60.5 mmol) in CHCl3 (500 mL) was treated with POCl3 (55 mL, 92 g, 602 mmol) over 15 min. The solution was refluxed 2 hours, cooled, poured onto ice (1500 mL) and the pH was adjusted to 12 with 20% NaOH (700 g). The separated aqueous layer was extracted with CHCl3 (2×200 mL). The extract was washed with H2O (2×200 mL), saturated NaHCO3 (20 mL), dried (MgSO4) and evaporated in vacuo to a white solid. Recrystallization from ethanol gave 23.2 g (75%) of 1st crop title compound, mp 227°-229° C. Further recrystallizations did not change the melting point.

Workup

  1. temperatureThe solution was refluxed 2 hours
  2. temperaturecooled
  3. additionpoured onto ice (1500 mL)
  4. extractionThe separated aqueous layer was extracted with CHCl3 (2×200 mL)
  5. washThe extract was washed with H2O (2×200 mL), saturated NaHCO3 (20 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo to a white solid
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-df691339492c4151bca46d7866c597c0
Source dataset
uspto-grants-1986_10
Patent number
US04617394

Reaction notes

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