Water → 3-(Acetylethylamino)-2-[1,1'-biphenyl]-4-yl-6-fluoro-4-quinolinecarboxylic acid

HRID 1073257Notes

Reaction equation

[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:16]([NH:17][CH2:18][CH3:19])=[C:15]([C:20]([OH:22])=[O:21])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([F:23])[CH:13]=3)[N:8]=2)=[CH:3][CH:2]=1.O.[C:31](OC(=O)C)(=[O:33])[CH3:32]>S(=O)(=O)(O)O>[C:31]([CH2:19][CH2:18][NH:17][C:16]1[C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:6][CH:5]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:20]([OH:22])=[O:21])=[CH:13][C:12]([F:23])=[CH:11][CH:10]=2)(=[O:33])[CH3:32]

Participants

Conditions

Temperature: 80 °C

Procedure

A 2.8 g portion of 2-[1,1'-biphenyl]-4-yl-3-(ethylamino)-6-fluoro-4-quinolinecarboxylic acid was suspended in 25 ml of acetic anhydride. To this suspension was added 5 drops of concentrated sulfuric acid, then the mixture was heated at 80° C. for 2 hours. The solution was cooled, added to 200 ml of water and stirred for 30 minutes. The resulting solid was collected, washed with water, then dichloromethane and dried at 110° C. in vacuo, giving 2.0 g of the desired product as a pale yellow solid, mp 260°-262° C.

Workup

temperatureThe solution was cooled
customThe resulting solid was collected
washwashed with water
dry with materialdichloromethane and dried at 110° C. in vacuo

Sources & evidence

ORD record: ord-4d49a91db2784a66863172342c4def78
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968702

Reaction notes

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