Sodium Hydroxide → (3,4-Dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methanol

HRID 1437328Notes

Reaction equation

HRID 1437328 reaction equation
O=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12](OC)=[O:13])=[N:11][C:4]=2[NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCOCC.C(Cl)(Cl)Cl>[S:6]1[CH2:7][CH2:2][NH:3][C:4]2[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:5]1=2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 21873660Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

Product 1

HCID 18454501(3,4-Dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methanolYield 59.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (1 g) (1.0 g) in dry tetrahydrofuran (170 ml) was treated with a 1M solution of lithium aluminium hydride in ether (14 ml) and the mixture was heated under reflux for 18 hours. It was cooled and a slight excess of 2N sodium hydroxide was added followed by chloroform and anhydrous sodium sulphate and the mixture was stirred for 30 minutes and filtered. The solution was evaporated to dryness to give a semi-solid (0.482 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureIt was cooled
  4. filtrationfiltered
  5. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-e8a6a32f0468407a9dc62649dd0f1127
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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