Hydrochloric Acid → 5-Methoxy-4-methyl-2-(pyrimidin-2-yl)benzoic acid

HRID 1477745Notes

Reaction equation

HRID 1477745 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:6]([CH3:21])=[CH:7][C:8]([C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11].Cl>CO.C1COCC1>[CH3:3][O:4][C:5]1[C:6]([CH3:21])=[CH:7][C:8]([C:15]2[N:16]=[CH:17][CH:18]=[CH:19][N:20]=2)=[C:9]([CH:14]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90422098Methyl 5-methoxy-4-methyl-2-(pyrimidin-2-yl)benzoate

Product 1

HCID 904221425-Methoxy-4-methyl-2-(pyrimidin-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1M aq. NaOH (4 mL) was added to a rt suspension of methyl 5-methoxy-4-methyl-2-(pyrimidin-2-yl)benzoate (503 mg, 1.95 mmol) in MeOH (5 mL) and THF (5 mL) and stirred at rt for 2 days. The residue was acidified with 25% aq. HCl, washed with DCM and concentrated in vacuo to yield the title compound A-1-16 as a off-white solid as its HCl-salt. LC-MS A: tR=0.63 min, [M+H]+=245.06.

Workup

  1. washwashed with DCM
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-379f90527b7c4ddc98ec7c6c5ceb46f1
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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