Sodium Hydroxide → 3-(4-Methoxy-1H-pyrazol-5-yl)-4-methylbenzoic acid

HRID 1488141Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13]C)=[O:12].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[N:5][NH:6][C:7]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([OH:13])=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-methoxy-1H-pyrazol-5-yl)-4-methylbenzoate (compound 244.6, 180 mg, 0.73 mmol) in methanol (4 mL). Sodium hydroxide (117 mg, 2.92 mmol) in water (2 mL) was added and the resulting solution was stirred for 3 h at 60° C., then concentrated under reduced pressure. The pH of the residue was adjusted to 1 with aqueous hydrogen chloride (1 M), then concentrated under reduced pressure. Methanol (5 mL) was added to the residue and the solids were filtered from the solution. The filtrate was concentrated under reduced pressure to obtain the title compound as a limit yellow solid (353 mg, crude).

Workup

customInto a 50-mL round-bottom flask, was placed
concentrationconcentrated under reduced pressure
concentrationconcentrated under reduced pressure
additionMethanol (5 mL) was added to the residue
filtrationthe solids were filtered from the solution
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-e565b459ca494b4caaae3d29ce9d7bc7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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