Methanol → HCID 22322123, compound

HRID 496597Notes

Reaction equation

HRID 496597 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14]CC)=[O:13])=[C:7]2[N:17]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]#[C:31][CH3:32])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH3:18].[OH-].[Na+].CO>O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([OH:14])=[O:13])=[C:7]2[N:17]([S:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]#[C:31][CH3:32])=[CH:26][CH:27]=1)(=[O:20])=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22322132HCID 22322132, compound2×

Product 1

HCID 22322123HCID 22322123, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 8-bromo-4-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-3-quinolinecarboxylate (0.52 g, 1.0 mmol), the product of Example 97, was treated with 1 N aqueous sodium hydroxide (1.1 mL) in 1:1 methanol:water (6 mL) to give 0.390 g of 8-bromo-4-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-3-quinolinecarboxylic acid as an off-white powder. Electrospray Mass Spec 489 and 490.9 (M+H)+

Sources & evidence

ORD record
ord-79dd92ad021b42ab8595dd1add979801
Source dataset
uspto-grants-2005_09
Patent number
US06946473B2

Reaction notes

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