Hydrochloric Acid → HCID 131720886, compound

HRID 399712Notes

Reaction equation

HRID 399712 reaction equation
C([O:3][C:4]([C:6]1([CH3:17])[C:11](=[O:12])[NH:10][C@@H:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]2[O:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[CH3:17][C:6]1([C:4]([OH:5])=[O:3])[C:11](=[O:12])[NH:10][C@@H:9]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]2[O:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131720887HCID 131720887, compound

Product 1

HCID 131720886HCID 131720886, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-ethyl-2-methyl-3-oxo-octahydro-2H-1,4-benzoxazine-2-carboxylate (4.80 g, 19.8 mmoles) and 1N NaOH (29,7 ml, 20.7 mmoles) in dioxan (80 ml) was stirred for 20 hours. The solvent was evaporated, 1N HCl (90 ml, 90 mmoles) was added to the residue and the mixture was extracted with ethyl acetate (4×60 ml). The organic phase was dried over MgSO4, the solvent was evaporated and the product was recrystallized from ethyl acetate. Thus there were obtained 2.3 g (54,5%) of the title product in the form of white crystals, m.p. 142°-144° C.

Workup

  1. customThe solvent was evaporated
  2. extractionthe mixture was extracted with ethyl acetate (4×60 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent was evaporated
  5. customthe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-98dc2e80186d46f6b04568bc95270dcd
Source dataset
uspto-grants-1998_10
Patent number
US05824652

Reaction notes

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