Methanol → Methyl 6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

HRID 2081551Notes

Reaction equation

HRID 2081551 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:11]=1.S(=O)(=O)(O)O.[CH3:20]O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:20])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 106086516-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid

Product 1

HCID 10633075Methyl 6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

Procedure

A mixture of 12 g of 6-chloro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid, 200 ml of methanol, and 10 ml of concentrated sulfuric acid was heat-refluxed for 24 hours with stirring. The liquid reaction mixture was concentrated in vacuo. To the residue were added an aqueous solution of sodium hydrogencarbonate and ethyl acetate, and the resulting organic layer was separated, washed with water, and dried over magnesium sulfate. The solvent was clitilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and ethanol to give 9.2 g of methyl 6-chloro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate. Melting point: 60°-61° C.

Workup

  1. temperaturewas heat-refluxed for 24 hours
  2. customThe liquid reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionTo the residue were added an aqueous solution of sodium hydrogencarbonate and ethyl acetate
  5. customthe resulting organic layer was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe residue was recrystallized from a mixed solvent of isopropyl ether and ethanol

Sources & evidence

ORD record
ord-470d2dde89944e539be49166bde7ab63
Source dataset
uspto-grants-1993_02
Patent number
US05185333

Reaction notes

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