Lithium Hydroxide → 2,6-Bis(4-cyanophenoxy)-nicotinic acid

HRID 1024680Notes

Reaction equation

HRID 1024680 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[N:9][C:8]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1)C>O.C1COCC1>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([O:22][C:8]2[N:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=3)[CH:11]=[CH:12][C:7]=2[C:6]([OH:31])=[O:5])=[CH:24][CH:25]=1)#[N:30]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67606024HCID 67606024, compound

Product 1

HCID 676059982,6-Bis(4-cyanophenoxy)-nicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.2 g (8.4 mmol) of lithium hydroxide was added to a stirred solution of 2,6-bis(4-cyano phenoxy)-nicotinic acid ethyl ester, 1.6 g (4.15 mmol), in a mixture of 5 ml of water and 2.5 ml of THF (2:1) at 5° C. and the contents were stirred for 3 h at RT. The reaction mixture was washed with diethylether. 6 N HCl was added to aqueous layer with stirring until the solution attained a pH of 2. The white precipitate obtained was collected, washed with water and dried under reduced pressure to afford 1.1 g of the required product. Percentage purity (LCMS): 83.2%, (M+1)=357.0+1. 1H NMR (DMSO-d6): δ 6.98 (1H, d), 7.26 (4H, d), 7.80 (4H, d), 13.22 (1H, brs).

Workup

  1. washThe reaction mixture was washed with diethylether
  2. addition6 N HCl was added to aqueous layer
  3. stirringwith stirring until the solution
  4. customThe white precipitate obtained
  5. customwas collected
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e5323bec0c614453a9d0fdc925bc7143
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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