Hydrochloric Acid → tert-Butyl 5-hydroxypyridine-3-carboxylate

HRID 1271638Notes

Reaction equation

HRID 1271638 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

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53432596tert-Butyl 5-hydroxypyridine-3-carboxylateYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-83fb9e9f22c24a64933b84fc6660f003
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Reaction notes

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