Sodium Hydroxide → 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid

HRID 2233335Notes

Reaction equation

HRID 2233335 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[CH2:9][S:8][C:7]2[CH:10]=[CH:11][C:12]([C:14]([O:16]C)=[O:15])=[N:13][C:6]=2[NH:5]1>O1CCOCC1.O>[O:3]=[C:4]1[CH2:9][S:8][C:7]2[CH:10]=[CH:11][C:12]([C:14]([OH:16])=[O:15])=[N:13][C:6]=2[NH:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21873660Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

Product 1

HCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.5 M NaOH solution (8 mL, 4 mmole) was added dropwise over 2 hr to a solution of methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (788 mg, 3.52 mmole) in dioxane (120 mL) and water (30 mL). The reaction was stirred overnight then was concentrated to about 3 mL. Water (5 mL) was added and the pH was adjusted to 4 with 2 M HCl. The precipitated solid was collected, washed with a small volume of water and dried under vacuum to give the title compound (636 mg, 86%) as a solid: MS (APCI−) m/e 209 (M−H)−, 165 (M-COOH)−.

Workup

  1. concentrationthen was concentrated to about 3 mL
  2. additionWater (5 mL) was added
  3. customThe precipitated solid was collected
  4. washwashed with a small volume of water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-17872ed1b7164c8c88dd3650e1b91494
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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