Sodium Hydroxide → 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)-morpholino]-2,3,5-trifluorobenzoic acid

HRID 477830Notes

Reaction equation

HRID 477830 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:8][CH:9]1[CH2:14][N:13]([C:15]2[C:25]([F:26])=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[C:17]([F:27])[C:16]=2[F:28])[CH2:12][CH2:11][O:10]1)[CH3:7])=[O:5])[CH3:2].[OH-].[Na+]>CO.O>[CH2:1]([O:3][C:4]([N:6]([CH2:8][CH:9]1[CH2:14][N:13]([C:15]2[C:25]([F:26])=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:27])[C:16]=2[F:28])[CH2:12][CH2:11][O:10]1)[CH3:7])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14652578ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoate

Product 1

HCID 146525794-[2-(N-ethoxycarbonyl-N-methylaminomethyl)-morpholino]-2,3,5-trifluorobenzoic acidYield 68.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 19.1 g of ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoate in 100 ml of methanol is added dropwise a solution of 7.56 g of sodium hydroxide in 100 ml of water under ice-cooling. After stirring under ice-cooling for 20 minutes, the methanol is distilled off under reduced pressure. The solution is washed with ethyl acetate, made acid with 6 N hydrochloric acid and then extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, the ethyl acetate is distilled off under reduced pressure. To the residue is added isopropyl ether. The obtained crystals are filtered with suction and dried to give 12.2 g of 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)-morpholino]-2,3,5-trifluorobenzoic acid in 68% yield, melting at 170°-172° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. distillationthe methanol is distilled off under reduced pressure
  4. washThe solution is washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe ethyl acetate is distilled off under reduced pressure
  8. additionTo the residue is added isopropyl ether
  9. filtrationThe obtained crystals are filtered with suction
  10. customdried

Sources & evidence

ORD record
ord-522c1812f3a8462fb293c4bd432c998f
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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