Hydrogen Bromide → HCID 178515075, compound

HRID 323645Notes

Reaction equation

Br.CS(O)(=O)=O.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12](=[O:32])[C:13]3[C:21](=[O:22])[N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=4)[N:19]=[C:18]([OH:31])[C:14]=3[NH:15][C:16]=2[CH:17]=1>>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12](=[O:32])[C:13]3[C:21](=[O:22])[N:20]([C:23]4[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=4)[N:19]=[C:18]([OH:31])[C:14]=3[NH:15][C:16]=2[CH:17]=1

Participants

Reactant 3

HCID 260Hydrogen Bromide

HCID 6395Methanesulfonic Acid

HCID 178492082HCID 178492082, compound

Product 1

HCID 178515075HCID 178515075, compound

Conditions

Temperature: 110 °C

Procedure

To a 50 mL solution of 5:1 48% HBr:methanesulfonic acid was added 7-chloro-4-hydroxy-2-(4-methoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (1.0328 g, 27.9 mM). The resulting suspension was heated to 110° C. over 3.5 hours. HPLC analysis afforded a total conversion to a new material. The suspension was cooled to room temperature and filtered through a Buchner funnel. The yellow solid was washed 2× with 100 mL portions of distilled water followed by 200 mL of a 1:1 solution of THF:ether. The material was then washed with hexanes until the yellow solid was free flowing. This solid was allowed to air dry for 72 hours prior to submission for analysis. No percent yield was recorded for this reaction.

Workup

customHPLC analysis afforded a total conversion to a new material
temperatureThe suspension was cooled to room temperature
filtrationfiltered through a Buchner funnel
washThe yellow solid was washed 2× with 100 mL portions of distilled water
washThe material was then washed with hexanes until the yellow solid
customto air dry for 72 hours
customNo percent yield
customwas recorded for this reaction

Sources & evidence

ORD record: ord-93d7a6e7c67d4febb3e163d097eed7e3
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214826B1

Reaction notes

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