Hydrochloric Acid → HCID 70009302, compound

HRID 1532040Notes

Reaction equation

HRID 1532040 reaction equation
[CH2:1]([O:3][C:4]1[C:8]([CH2:9][N:10]2C(=O)C3=CC=CC=C3C2=O)=[C:7]([C:21]([O:23]CC)=[O:22])[O:6][N:5]=1)[CH3:2].[ClH:26]>[OH-].[Na+]>[ClH:26].[NH2:10][CH2:9][C:8]1[C:4]([O:3][CH2:1][CH3:2])=[N:5][O:6][C:7]=1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10736209HCID 10736209, compound

Product 1

HCID 70009302HCID 70009302, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 3-ethoxy-4-phthalimidomethylisoxazole-5-carboxylate in 1 M NaOH was boiled under reflux for 45 min. The mixture was cooled, added concd HCl and extracted with diethylether (3×400 ml). The organic extracts were concentrated in vacuo, added 1 M HCl (600 mL) and boiled under reflux for 1 h. After cooling the mixture was washed with diethylether (3×600 mL) and concentrated in vacuo to give a crude product which was recrystallized (acetic acid) to yield the title compound (1.5 g, 82%): mp 215-216° C. (dec).

Workup

  1. temperatureunder reflux for 45 min
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethylether (3×400 ml)
  4. concentrationThe organic extracts were concentrated in vacuo
  5. additionadded 1 M HCl (600 mL)
  6. temperatureunder reflux for 1 h
  7. temperatureAfter cooling the mixture
  8. washwas washed with diethylether (3×600 mL)
  9. concentrationconcentrated in vacuo
  10. customto give a crude product which
  11. customwas recrystallized (acetic acid)

Sources & evidence

ORD record
ord-9ff91bce55224d808aa096a56d60e286
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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