Water → HCID 14771559, compound

HRID 329719Notes

Reaction equation

HRID 329719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]C)=[O:16])[C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[NH:7][C:6]=2[CH:14]=1.[CH3:19]C(C)([O-])C.[K+].CI.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[O:10][C:9]([CH3:11])([CH3:12])[C:8](=[O:13])[N:7]([CH3:19])[C:6]=2[CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14771558HCID 14771558, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14771559HCID 14771559, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.2 g of methyl 6-chloro-3,4-dihydro-2,2-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate in 20 ml of dimethylformamide is added 2.27 g of potassium t-butoxide, and the solution stirred at room temperature for 30 minutes. To the resultant solution is added dropwise a solution of 2.95 g of methyl iodide in 5 ml of dimethylformamide, and the solution stirred for 2.5 hours. To the resulting solution are added water and ethyl acetate to separate the organic layer followed by washing with water and drying over magnesium sulfate. After the solvent is distilled off under reduced pressure, to the residue are added 50 ml of ethanol and 50 ml of diluted aqueous sodium hydroxide solution and the system stirred at room temperature for 15 hours. To the resultant solution is added diluted hydrochloric acid and the precipitated crystals are collected by filtration and dried to give 3.9 g of 6-chloro-3,4-dihydro-2,2,4-trimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid, melting at 235°-236° C.

Workup

  1. stirringthe solution stirred for 2.5 hours
  2. customto separate the organic layer
  3. washby washing with water
  4. dry with materialdrying over magnesium sulfate
  5. distillationAfter the solvent is distilled off under reduced pressure, to the residue
  6. additionare added 50 ml of ethanol and 50 ml of diluted aqueous sodium hydroxide solution
  7. stirringthe system stirred at room temperature for 15 hours
  8. additionTo the resultant solution is added diluted hydrochloric acid
  9. filtrationthe precipitated crystals are collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-a9828af0efd047dbac8d93f5b0d4d583
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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