Hydrochloric Acid → 5-Methyl-6-(2-methylpiperidin-1-yl)nicotinic acid
Reaction equation
[CH3:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#N.[OH-:17].[K+].Cl.[OH2:20]>>[CH3:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]([OH:20])=[O:17]Participants
5
Procedure
A mixture of 5-methyl-6-(2-methylpiperidin-1-yl)nicotinonitrile (1 g; 4.64 mmol; 1 eq.) and potassium hydroxide (1.3 g; 23.2 mmol; 5 eq.) in water (60 mL) was stirred at reflux for 16 hours. The pH was adjusted to 5-6 with HCl 1M and the aqueous layer extracted with ethyl acetate. The combined organic phase was dried over magnesium sulphate and concentrated in vacuo to afford the title compound (1.1 g, 100%) as a yellow oil.
Workup
- temperatureat reflux for 16 hours
- extractionthe aqueous layer extracted with ethyl acetate
- dry with materialThe combined organic phase was dried over magnesium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b7010f80ee3f4bffa8fac792d95bcaa3
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889668B2
Reaction notes
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