Lithium Hydroxide → HCID 57500673, compound

HRID 2420967Notes

Reaction equation

HRID 2420967 reaction equation
[O:1]=[C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17]C)=[O:16])=[CH:5][C:4]=2[NH:3]1.[Li+].[OH-].C1COCC1.[OH-].[Na+]>O.CO>[O:1]=[C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([OH:17])=[O:16])=[CH:5][C:4]=2[NH:3]1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57500672HCID 57500672, compound

Product 1

HCID 57500673HCID 57500673, compoundYield 2.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate (35 mg, 0.12 mmol) and LiOH (60 mg, 0.83 mmol) were stirred in a (1:1:1, v:v:v) mixture of THF, MeOH and water (0.6 ml) for 2 hours. 6N aqueous NaOH was added and the solution filtered through celite. The solution was acidified and the resulting solid filtered. Preparative HPLC purification and genevac evaporation provided 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylic acid as a white solid (0.8 mg). LCMS (ES): 95% pure, m/z 247 [M+1]+.

Workup

  1. filtrationthe solution filtered through celite
  2. filtrationthe resulting solid filtered
  3. customPreparative HPLC purification and genevac evaporation

Sources & evidence

ORD record
ord-e9766d48185b497c9db480d2523cf30e
Source dataset
uspto-grants-2011_06
Patent number
US07956064B2

Reaction notes

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