Hydrochloric Acid → 3-(Pyridin-3-yloxy)benzoic acid

HRID 2401494Notes

Reaction equation

HRID 2401494 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#N)[CH:2]=1.[OH-:16].[Na+].Cl.C[OH:20].C(Cl)Cl>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]([OH:20])=[O:16])[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 578393623-(Pyridin-3-yloxy)benzonitrile

Product 1

HCID 185485043-(Pyridin-3-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 (571 mg, 2.91 mmol, 1.00 eq) was dissolved in ethanol (12 mL) and 1N NaOH (6 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 1N HCl (6 mL) and the reaction was concentrated in vacuo. The crude reaction was dissolved in 10% MeOH/CH2Cl2 and the undissolved salt was filtered off and the solvents were removed in vacuo to afford the title compound as a pale-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.47 (d, J=2.4 Hz, 1H), 8.44 (d, J=4.7 Hz, 1H), 7.75 (d, J=7.7 Hz, 1H), 7.60-7.48 (m, 4H), 7.36 (dd, J=8.0, 1.9 Hz, 1H)); ES-MS [M+1]+: 216.1.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. temperatureafter cooling the reaction
  3. concentrationthe reaction was concentrated in vacuo
  4. customThe crude reaction
  5. filtrationthe undissolved salt was filtered off
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-783209a1b1a14624be89e6ce5dbf5824
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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