Hydrochloric Acid → Tert-butyl 5-hydroxypyridine-3-carboxylate
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[N:6][CH:5]=1.[CH3:12][C:13]([CH3:16])([O-:15])[CH3:14].[K+].C(O)(C)(C)C.Cl>C1COCC1>[C:13]([O:15][C:3](=[O:2])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[N:6][CH:5]=1)([CH3:16])([CH3:14])[CH3:12]Participants
6
Procedure
5-Hydroxy-nicotinic acid methyl ester (1 g, 5.99 mmol) and potassium t-butoxide (4 g, 36 mmol) was stirred in THF (10 mL) and t-butanol (10 mL) at room temperature overnight. 1N HCl was added to adjust pH˜7 and the mixture was extracted with EtOAc (3×). The combined extracts were dried (Na2SO4), concentrated and purified by column chromatography to give the product (400 mg, 34%). MS (DCI) m/z 196 (M+H)+.
Workup
- customat room temperature
- customovernight
- extractionthe mixture was extracted with EtOAc (3×)
- dry with materialThe combined extracts were dried (Na2SO4)
- concentrationconcentrated
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-83fb9e9f22c24a64933b84fc6660f003
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07205409B2
Reaction notes
Loading…