Ethanol → 2-Fluoro-5-[(8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

HRID 1091805Notes

Reaction equation

[F:1][C:2]1C=[CH:8][C:7]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:21][CH3:22])[C:14](=[O:23])[NH:13][N:12]=2)=[CH:6][C:3]=1C#N.[OH-:24].[K+].[CH2:26]([OH:28])[CH3:27]>O>[F:1][C:2]1[CH:3]=[CH:6][C:7]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:21][CH3:22])[C:14](=[O:23])[NH:13][N:12]=2)=[CH:8][C:27]=1[C:26]([OH:24])=[O:28]

Participants

Conditions

Temperature: 100 °C

Procedure

2-fluoro-5-((8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile (124) (2.7 g, 8.73 mmol) and potassium hydroxide (4.90 g, 87.30 mmol) were added to ethanol (20 mL) and water (50 mL) and heated at 100° C. for 5 hours. The ethanol was evaporated off and the aqueous was extracted with ethyl acetate (1×75 mL). The aqueous was then acidified to pH1 with conc HCl to afford a solid, this was filtered, washed with water and dried to afford the desired material as a white solid (2.370 g, 83%); 1H NMR (400.132 MHz, DMSO) δ 3.82 (3H, s), 4.40 (2H, s), 7.16-7.23 (1H, m), 7.40-7.46 (2H, m), 7.64-7.68 (1H, m), 7.76 (1H, t), 7.84-7.88 (1H, m), 12.96-13.28 (1H, m), 12.59-12.63 (1H, m).

Workup

customThe ethanol was evaporated off
extractionthe aqueous was extracted with ethyl acetate (1×75 mL)
customto afford a solid
filtrationthis was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-8ee2403203234e69b5588cc0415b7e40
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129380B2

Reaction notes

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