Hydrochloric Acid → HCID 18617683, compound

HRID 1264219Notes

Reaction equation

HRID 1264219 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>C1COCC1.CO.CCOCC>[CH3:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18617593HCID 18617593, compound

Product 1

HCID 18617683HCID 18617683, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of Methyl 2-methyl-4-(2-methoxypyridin-5-yl)-benzoate (600 mg, 2.6 mmol) (reference example 34a) in THF/MeOH (8 mL, 1/1) is added NaOH (3 mL, 1M). The resulting mixture is stirred for 12 hours then acidified with hydrochloric acid (2M, to give pH 5). The mixture is diluted with ether then washed with brine, dried over MgSO4 and concentrated. The residual solid is triturated with ether/hexane (1/20). The resulting product (500 mg) is used without further purification. 1H NMR (CDCl3) d 2.71 (s, 3H), 3.98 (s, 3H), 6.82 (d, J=8 Hz, 1H), 7.41 (m, 2H), 7.81 (dd, J=8, 2 Hz, 1H), 8.13 (d, J=8 Hz, 1H), 8.43 (d, J=2 Hz, 1H). MS (EI) m/z 243 (M+).

Workup

  1. washthen washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residual solid is triturated with ether/hexane (1/20)
  5. customThe resulting product (500 mg) is used without further purification

Sources & evidence

ORD record
ord-03b79c1542b046f1aa506f4ad0955ed8
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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