Ethanol → 3-[(8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

HRID 1091798Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][C:13]1[CH:14]=C([CH:18]=[CH:19][CH:20]=1)C#N)=[N:9][NH:8][C:7]2=[O:21].[OH-:22].[K+].[CH2:24]([OH:26])[CH3:25]>O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][C:13]1[CH:14]=[C:25]([CH:18]=[CH:19][CH:20]=1)[C:24]([OH:22])=[O:26])=[N:9][NH:8][C:7]2=[O:21]

Participants

Conditions

Temperature: 100 °C

Procedure

3-((8-chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile (117) (3.75 g, 12.68 mmol) and potassium hydroxide (7.11 g, 126.81 mmol) were added to ethanol (30 mL) and water (70 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 beige solid (3.81 g, 95% yield); 1H NMR (400.132 MHz, DMSO) δ 4.67 (2H, s), 7.42-7.41 (2H, m), 7.72 (1H, s), 7.79-7.76 (1H, m), 7.81 (1H, t), 7.97 (1H, dd), 8.34 (1H, dd), 12.88 (1H, s); m/z (LC-MS, ESI+), RT=0.92 (M+H 315).

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-87fd6dcf13004886b8f3824580e6d1b9
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129380B2

Reaction notes

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