Ethanol → 3-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzoic acid

HRID 1091809Notes

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]=[C:19]([F:21])[CH:20]=1)C#N)=[N:9][NH:8][C:7]2=[O:22].[OH-:23].[K+].[CH2:25]([OH:27])[CH3:26]>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:26]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:25]([OH:23])=[O:27])=[N:9][NH:8][C:7]2=[O:22]

Participants

Conditions

Temperature: 100 °C

Procedure

3-((8-chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzonitrile (127) (1.26 g, 4.02 mmol) and potassium hydroxide (2.253 g, 40.16 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 compound as a beige solid (1.280 g, 96% yield); 1H NMR (400.132 MHz, DMSO) δ 4.69 (2H, s), 7.35 (1H, d), 7.50 (1H, d), 7.58 (1H, s), 7.82 (1H, t), 7.99 (1H, d), 8.34 (1H, d), 12.87 (1H, s); m/z (LC-MS, ESI+), RT=0.99 (M+H 333).

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-30fe82f3ead7408e927b7bb1a2dd14be
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129380B2

Reaction notes

Loading…