Acetic Acid → HCID 18523349, compound

HRID 413056Notes

Reaction equation

[OH-].[K+].[F:3][C:4]1[C:17]2[N:16]=[CH:15][C:14]3[N:13]([CH3:18])[CH:12]=[C:11]([C:19]([O:21]CC)=[O:20])[C:10](=[O:24])[C:9]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[N:25]1[CH2:30][CH2:29][C:28]([OH:41])([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[CH2:27][CH2:26]1.C(O)(=O)C>C(O)C.O>[F:3][C:4]1[C:17]2[N:16]=[CH:15][C:14]3[N:13]([CH3:18])[CH:12]=[C:11]([C:19]([OH:21])=[O:20])[C:10](=[O:24])[C:9]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[N:25]1[CH2:30][CH2:29][C:28]([OH:41])([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

0.86 cm3 of 1 N aqueous potassium hydroxide was added, with stirring, to a suspension of 0.39 g of ethyl 7-fluoro-8-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl]-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate in 4.5 cm3 of ethanol and 3.5 cm3 of water. The mixture was heated at about 80° C. for 3 hours, and then after cooling, 20 cm3 of water were added and then the medium was acidified with 0.05 cm3 of acetic acid. The precipitate was filtered off, dewatered, washed with 2 cm3 of isopropanol and then washed twice with 2 cm3 of diisopropyl ether and dried. 0.25 g of 7-fluoro-8-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl]-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid was obtained in the form of a yellow solid, which melted above 260° C.

Workup

temperatureafter cooling
filtrationThe precipitate was filtered off
washwashed with 2 cm3 of isopropanol
washwashed twice with 2 cm3 of diisopropyl ether
customdried

Sources & evidence

ORD record: ord-b4e30657ef3b4c7794d0e75396f67cae
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566362B2

Reaction notes

Loading…