Sodium Hydroxide → 2-(Benzo[d]oxazol-2-yl)nicotinic acid

HRID 1400237Notes

Reaction equation

HRID 1400237 reaction equation
[OH-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[N:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([O:16]CC)=[O:15]>CCO>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[N:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67540260Ethyl 2-(benzo[d]oxazol-2-yl)nicotinate

Product 1

HCID 675405322-(Benzo[d]oxazol-2-yl)nicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaOH (1.65 mL, 2M in water) was added to a solution of ethyl 2-(benzo[d]oxazol-2-yl)nicotinate (290 mg, 0.973 mmol) in EtOH. After stirring for 3 h at room temperature the solvent was removed in vacuo. The residue was dissolved in water (4 mL) and dilute HCl (1.8 mL, 2M in water) was added resulting in pH 2-3 of the mixture. The mixture was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous NaCl solution and dried over MgSO4. Removal of the solvent provided the title compound (190 mg, 81%); ESI-MS [M+H+]=241.1.

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in water (4 mL)
  3. additiondilute HCl (1.8 mL, 2M in water) was added

Sources & evidence

ORD record
ord-5ae51abd7b2042dfaa112115988f8ffd
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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