Water → HCID 10681590, compound

HRID 2081552Notes

Reaction equation

HRID 2081552 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:11]=1.[C:16](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][N:7]([CH3:16])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10633075Methyl 6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

Product 1

HCID 10681590HCID 10681590, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 9.2 g of methyl 6-chloro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate and 6.7 g of potassium carbonate in 100 ml of dimethylformamide was added 6.4 g of methyl iodide with cooling and stirring. The resulting mixture was heated at 70° C. for 2 hours with stirring. The liquid reaction mixture was added to 200 ml of water, and the resulting insoluble substance was filtered off, washed with water, and dried, thereby obtaining 7.1 g of methyl 6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate. Melting point: 91°-92° C.

Workup

  1. temperaturewith cooling
  2. stirringwith stirring
  3. customThe liquid reaction mixture
  4. filtrationthe resulting insoluble substance was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ec90729c1afc4a5489a7f8a52b63b0ce
Source dataset
uspto-grants-1993_02
Patent number
US05185333

Reaction notes

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