Sodium Hydroxide → HCID 10043588, compound

HRID 1647461Notes

Reaction equation

HRID 1647461 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][O:18]C(=O)C1C=CC=CC=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[C:30]([CH3:35])[CH:29]=1.[OH-].[Na+]>O1CCOCC1.CO>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:32][C:31]1[CH:33]=[CH:34][C:28]([F:27])=[CH:29][C:30]=1[CH3:35])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:17][OH:18])(=[O:5])[CH:2]([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 679824-Fluoro-2-methylanilineHCID 10384366HCID 10384366, compound

Product 1

HCID 10043588HCID 10043588, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-isobutyryl-4-chloro-8-(benzoyloxymethyl)quinoline (1.84 g, 5 mmol) and 4-fluoro-2-methylaniline (0.78 ml, 7 mmol) in dioxan (25 ml) was heated at reflux for 2 hours, then the solvent evaporated. A solution of sodium hydroxide (0.8 g, 20 mmol) in methanol (50 ml) was added and the mixture stirred at room temperature for 1.5 hours. The resulting precipitate was filtered off and recrystallised from methanol to give (0.48 g, 27%), m.p. 139°-140°.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent evaporated
  3. filtrationThe resulting precipitate was filtered off
  4. customrecrystallised from methanol
  5. customto give (0.48 g, 27%), m.p. 139°-140°

Sources & evidence

ORD record
ord-283f4b225f1f446cb391f748e3b23f27
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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