Water → methyl 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate

HRID 329712Notes

Reaction equation

HRID 329712 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.[CH3:18]C(C)([O-])C.[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:18])[C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14517232methyl 6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14517233methyl 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4.85 g of methyl 6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate in 30 ml of dimethylformamide is added 2.7 g of potassium t-butoxide and solution stirred at room temperature for 30 minutes. To the resultant solution is added dropwise a solution of 3.4 g of methyl iodide in 10 ml of dimethylformamide under stirring. After the reaction solution is stirred for 1.5 hours, 200 ml of water is added thereto. The insoluble substance is collected by filtration, washed with water and dried to give 5.1 g of methyl 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate, melting at 128°-130° C.

Workup

  1. stirringunder stirring
  2. stirringAfter the reaction solution is stirred for 1.5 hours
  3. filtrationThe insoluble substance is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ac25233644c04faf8123f0fef24e646d
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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