Lithium Hydroxide → 4,6-Dichloronicotinic acid

HRID 2376704Notes

Reaction equation

HRID 2376704 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[N:6][CH:5]=1.[Li+].[OH-]>C1COCC1.O>[Cl:10][C:9]1[C:4]([C:3]([OH:12])=[O:2])=[CH:5][N:6]=[C:7]([Cl:11])[CH:8]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 2764083Methyl4,6-dichloronicotinate

Product 1

HCID 8171584,6-Dichloronicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4,6-Dichloro-nicotinic acid methyl ester (27.3 g, 133 mmol) was dissolved in THF (150 mL). LiOH (3.53 g, 147 mmol), dissolved in H2O (25 mL), was added dropwise and the reaction was allowed to stir for 18 h. The volatiles were removed in vacuo. The resultant residue was diluted with H2O (100 mL) and acidified with 6 N HCl while swirling at 0° C. The solution was brought to a pH of 2.0 and a yellow precipitate formed. The mixture was allowed to stand at 0° C. for 1 h then filtered to afford 4,6-dichloro-nicotinic acid as a yellow solid (20.6, 81%).

Workup

  1. additionwas added dropwise
  2. customThe volatiles were removed in vacuo
  3. additionThe resultant residue was diluted with H2O (100 mL)
  4. customwhile swirling at 0° C
  5. customa yellow precipitate formed
  6. waitto stand at 0° C. for 1 h
  7. filtrationthen filtered

Sources & evidence

ORD record
ord-451d362186f5445b98e0754ce8a997fb
Source dataset
uspto-grants-2008_12
Patent number
US07468382B2

Reaction notes

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