Lithium Hydroxide → HCID 86710327, compound

HRID 1398324Notes

Reaction equation

HRID 1398324 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[C:14]([C:15]([O:17]C)=[O:16])=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:4]([F:19])[CH:3]=1.[Li+].[OH-]>O.C1COCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:4]([F:19])[CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86710328HCID 86710328, compound

Product 1

HCID 86710327HCID 86710327, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl 4-(4-chloro-2,5-difluorophenyl)nicotinate (400 mg, 1.41 mmol) in water:THF (1:1, 8 mL) was added LiOH (67.5 mg, 2.82 mmol) and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was quenched with water (5 mL) and washed with ethyl acetate (2×5 mL). The aqueous layer was separated and acidified with 1.5N HCl and concentrated under reduced pressure to afford 4-(4-chloro-2,5-difluorophenyl)nicotinic acid (180 mg, 0.541 mmol, 38% yield) as a solid. LC/MS (ESI) m/e 270 [(M+H)+, calcd for C12H7ClF2NO2 270]; LC/MS retention time (method B): tR=1.48 min.

Workup

  1. customThe reaction mixture was quenched with water (5 mL)
  2. washwashed with ethyl acetate (2×5 mL)
  3. customThe aqueous layer was separated
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1535160c92374b26ac8d83ee3a1630e0
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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