Potassium Hydroxide → HCID 67207835, compound
Reaction equation
C([O:3][C:4](=[O:18])[C:5]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:8]([C:14]([CH3:17])([CH3:16])[CH3:15])=[N:7][CH:6]=1)C.[OH-].[K+]>C(O)C.O>[C:14]([C:8]1[CH:9]=[C:10]([O:11][CH2:12][CH3:13])[C:5]([C:4]([OH:18])=[O:3])=[CH:6][N:7]=1)([CH3:17])([CH3:15])[CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
6-tert-Butyl-4-ethoxy-nicotinic acid ethyl ester (100 mg, 0.4 mmol) was dissolved in ethanol. Potassium hydroxide (46 mg, 0.8 mmol) in 1 mL of water was added. It was stirred at 80° C. for 1 hr, checked by thin layer chromatography and LC-MS until the reaction was completed. The mixture was concentrated at high vacuum and dried overnight to give 6-tert-butyl-4-ethoxy-nicotinic acid as a white solid which was used in the next reaction with out further purification. The 6-tert-butyl-4-ethoxy-nicotinic acid was heated at 70° C. in 3 mL of SOCl2 for 2 hrs. The reaction mixture containing 6-tert-butyl-4-ethoxy-nicotinoyl chloride was concentrated to dryness then suspended in tetrahydrofuran (6 mL) with 0.1 mL of triethylamine and used for the next reaction immediately.
Workup
- concentrationThe mixture was concentrated at high vacuum
- customdried overnight
Sources & evidence
- ORD record
- ord-9a1613212f2842a5b33a9ada98b679d8
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513239B2
Reaction notes
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