Hydrochloric Acid → 2-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

HRID 269966Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[O:12]2)=[CH:6][C:3]=1[C:4]#N.[OH-:21].[Na+].[OH2:23].[NH2:24][NH2:25].Cl>O>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:12])[NH:25][N:24]=2)=[CH:6][C:3]=1[C:4]([OH:23])=[O:21]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 2-fluoro-5-(3-oxo-3H-isobenzofuran-1-ylidenemethyl)benzonitrile in water (200 ml) was added aqueous sodium hydroxide (26.1 g in 50 ml water) solution and the reaction mixture was heated under nitrogen to 90° C. for 30 minutes. The reaction mixture was partially cooled to 70° C., and hydrazine hydrate (100 ml) was added and stirred for 18 hours at 70° C. The reaction was cooled to room temperature and acidified with 2M HCl to pH 4. The mixture was stirred for 10 min and filtered. The resulting solid was washed with water, hexane, ether, ethyl acetate and dried to yield 2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)benzoic acid as a pale pink powder (30.0 g, 77%). m/z [M+1]+ 299 (96% purity), δH 4.4 (2H, s), 7.2-7.3 (1H, m), 7.5-7.6 (1H, m), 7.8-8.0 (4H, m), 8.2-8.3 (1H, m), 12.6 (1H, s).

Workup

temperatureThe reaction mixture was partially cooled to 70° C.
temperatureThe reaction was cooled to room temperature
stirringThe mixture was stirred for 10 min
filtrationfiltered
washThe resulting solid was washed with water, hexane, ether, ethyl acetate
customdried

Sources & evidence

ORD record: ord-91a93cd9199f4ab0ab7413e7d7ff1bfe
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449464B2

Reaction notes

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