Sodium Hydroxide → HCID 10043588, compound

HRID 1534481Notes

Reaction equation

HRID 1534481 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-benzoyloxymethylquinoline (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 recrystallized 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. customrecrystallized from methanol
  5. customto give (0.48 g, 27%), m.p. 139°-140°

Sources & evidence

ORD record
ord-113c4a8962444042b7ab0949e43a9e1b
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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