Lithium Hydroxide → HCID 21076072, compound

HRID 1374455Notes

Reaction equation

HRID 1374455 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CO[C:19](=O)[CH:20]1[CH2:25][CH:24](I)CCN1.[OH-].[Li+]>CN(C=O)C.C1COCC1>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1)[CH2:20][CH2:25][CH3:24]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 69471455HCID 69471455, compoundHCID 178524611HCID 178524611, compound

Product 1

HCID 21076072HCID 21076072, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 4-hydroxypyridine-2-carboxylic acid (200 mg, 1.4 mmol) in DMF (2 mL), potassium carbonate (397 mg, 2.8 mmol) was added followed by n-bromobutane (197 mg, 1.4 mmol), warmed at 60° C. for overnight. The solvent was removed to obtain the crude ester product. The crude ester (360 mg, 1.4 mmol) was dissolved in THF (4 mL), lithium hydroxide (72 mg, 1.7 mmol) was added, and the reaction mixture stirred at room temperature for 2 h. The residue obtained on removal of solvent was purified by silica gel chromatography using 10% MeOH in DCM to provide 4-butoxypyridine-2-carboxylic acid 15a (R10=butyl) (100 mg, 43%). 1H NMR (300 MHz, CD3OD) δ 8.37 (d, J=6.0, 1), 7.63 (d, J=2.7, 1), 7.07 (dd, J=2.7, 6.0, 1), 4.15 (t, J=6.6, 2), 1.82 (m, 2), 1.54 (m, 2), 1.01 (t, J=7.5, 3). MS (ES−): 194 (M−1).

Workup

  1. customThe solvent was removed
  2. customto obtain the crude ester product
  3. customThe residue obtained on removal of solvent
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-0d70ae68612540dab41118db18dd25e8
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

Loading…