Hydrochloric Acid → HCID 67292189, compound
Reaction equation
O[C:2]1[CH:3]=[C:4]([C:8]#N)[CH:5]=[N:6]C=1.C[Li].S(=O)(=O)(O)[OH:13].Cl.[Cl-].[Na+].CC[O:22][CH2:23][CH3:24]>C1COCC1>[C:3]([C:4]1[CH:8]=[C:23]([OH:22])[CH:24]=[N:6][CH:5]=1)(=[O:13])[CH3:2]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1.8 g (14.98 mM) of 5-hydroxy-3-pyridinecarbonitrile in 120 ml of THF is added dropwise to a 1.6 M solution of methyllithium in ether (18.7 ml, 29.92 mM), cooled to 0° C. After stirring for 15 minutes, the reaction medium is allowed to warm up to room temperature and stirring is continued for 2 hours. 50 ml of 0.5 N sulfuric acid solution are added to the reaction medium and the pH of the medium is then brought to 6 by adding concentrated hydrochloric acid solution (10 N). The aqueous phase is saturated with sodium chloride and then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The product obtained is then washed with ether and filtered off to give the desired product in the form of a yellow powder with a yield of 75%.
Workup
- temperatureto warm up to room temperature
- stirringstirring
- waitis continued for 2 hours
- extractionextracted with ethyl acetate
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe product obtained
- washis then washed with ether
- filtrationfiltered off
Sources & evidence
- ORD record
- ord-7b8cdb10fe734151ad783f9e3ac9654a
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148407B2
Reaction notes
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