Benzylamine → 5-Flouro-8-hydroxy-N-(phenylmethyl)-7-quinolinesulfonamide

HRID 2301442Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([S:12](Cl)(=[O:14])=[O:13])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.C(O)(=O)C.O>[F:1][C:2]1[CH:11]=[C:10]([S:12]([NH:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:14])=[O:13])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: -78 °C

Procedure

A suspension of 5-fluoro-8-hydroxy-7-quinolinesulfonyl chloride (0.150 g) in 2 mL of THF is cooled to −78° C. and treated with benzylamine (0.186 mL). The mixture is allowed to warm to 25° C. over several hours, then diluted with 50 μL of glacial acetic acid and 2 mL of distilled water. The oil which forms is crystallized by scratching, and the resulting suspension is stirred for one hour. The solid is filtered, washed with two 2 mL portions of distilled water and dried in a stream of air to give 0.121 g of the title compound as a solid.

Workup

temperatureto warm to 25° C. over several hours
customThe oil which forms is crystallized
filtrationThe solid is filtered
washwashed with two 2 mL portions of distilled water
customdried in a stream of air

Sources & evidence

ORD record: ord-3bacd45b6cc84870bdd8d96179a23c41
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500842B1

Reaction notes

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