Sodium Hydroxide → 2,4-Dichloro-5-(5-fluoropyridin-2-yl)benzoic acid hydrochloride

HRID 522134Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of methyl 2,4-dichloro-5-(5-fluoropyridin-2-yl)benzoate (Preparation 34, 1 g, 3.33 mmol) in methanol (20 mL) was added 2M aqueous sodium hydroxide solution (3.3 mL, 6.66 mmol) and the reaction was heated at 50° C. for 1 hour. The reaction was concentrated in vacuo and the residue stirred with 2M aqueous hydrochloric acid (30 mL). The resulting precipitate was filtered, washed with water and dried in vacuo to afford the title compound as a white solid (900 mg, 84%).

Workup

concentrationThe reaction was concentrated in vacuo
filtrationThe resulting precipitate was filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-190d56e47de345b68d69781470b78473
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328096B2

Reaction notes

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