Hydrochloric Acid → 4'-Methyl-5-(pyridin-2-yloxy)biphenyl-3-carboxylic acid

HRID 1845275Notes

Reaction equation

HRID 1845275 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([O:23]C)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58188387Methyl 4'-methyl-5-(pyridin-2-yloxy)biphenyl-3-carboxylate

Product 1

HCID 581881514'-Methyl-5-(pyridin-2-yloxy)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4′-methyl-5-(pyridin-2-yloxy)biphenyl-3-carboxylate (460 mg, 1.4 mmol) in tetrahydrofuran (20 mL) was added 2.5 M aqueous lithium hydroxide solution (5.6 mL, 14 mmol). After being stirred at room temperature overnight, the mixture was acidified to pH=5 by addition of 2N aq. HCl and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (CD3OD, 300 MHz): 8.17 (d, 1H, J=3.2 Hz), 8.11 (s, 1H), 7.88 (td, 1H, J=8.0, 2.0 Hz), 7.65 (s, 1H), 7.58-7.52 (m, 3H), 7.29 (d, 2H, J=8.4 Hz), 7.16 (dd, 1H, J=7.2, 4.8 Hz), 7.06 (d, 1H, J=8.0 Hz), 2.38 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e94b7c895a3c49d48041d46114ff2f54
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…