Lithium hydroxide, monohydrate → HCID 68276429, compound

HRID 334394Notes

Reaction equation

HRID 334394 reaction equation
O.[OH-].[Li+].[NH2:4][C:5]1[N:15]=[C:14]([S:16][CH3:17])[C:13]([C:18]#[N:19])=[CH:12][C:6]=1[C:7]([O:9]CC)=[O:8]>C(O)C.O>[NH2:4][C:5]1[N:15]=[C:14]([S:16][CH3:17])[C:13]([C:18]#[N:19])=[CH:12][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12006384HCID 12006384, compound

Product 1

HCID 68276429HCID 68276429, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3.08 g (2 eq) of lithium hydroxide monohydrate is added at room temperature to a solution of 8.7 g (36.7 mmol) of ethyl 2-amino-5-cyano-6-(methylthio)nicotinate in 87 ml of ethanol and 87 ml of water. The reaction mixture is stirred at 60° C. for 2 hours. The ethanol is evaporated and 1 N aqueous soda is added. The aqueous phase is washed with ethyl acetate and then re-acidified by adding 1 N aqueous hydrogen chloride (pH=1). The precipitate formed is filtered, rinsed with water and with diethyl ether and then dried under vacuum to yield 7.67 g (quantitative) of 2-amino-5-cyano-6-(methylthio)nicotinic acid in the form of a brown powder.

Workup

  1. customThe ethanol is evaporated
  2. addition1 N aqueous soda is added
  3. washThe aqueous phase is washed with ethyl acetate
  4. additionre-acidified by adding 1 N aqueous hydrogen chloride (pH=1)
  5. customThe precipitate formed
  6. filtrationis filtered
  7. washrinsed with water and with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-06b5a1a0f21b41f8815f21985c78bfc0
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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