Water → HCID 22142213, compound

HRID 1825656Notes

Reaction equation

HRID 1825656 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15]COCC[Si](C)(C)C)[C:12]2[C:7](=[C:8]([Br:26])[CH:9]=[C:10]([O:24][CH3:25])[CH:11]=2)[N:6]=1)=[O:4].O1CCCC1.O.O.[OH-].[Li+]>CO>[Br:26][C:8]1[CH:9]=[C:10]([O:24][CH3:25])[CH:11]=[C:12]2[C:7]=1[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:14][C:13]2=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23533344HCID 23533344, compound

Product 1

HCID 22142213HCID 22142213, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a light brown solution of 8-bromo-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester (Reference Example 24c) (4.98 g, 11.3 mmol) in 75 mL 3:1:1 tetrahydrofuran:methanol:water was added lithium hydroxide monohydrate (1.367 g, 32.6 mmol). The reaction was stirred at room temperature for 5 hours. The reaction mixture was concentrated and then poured into water. The solution was acidified to pH 2 with 1 N HCl and the resulting solids were isolated by filtration. The solids were then suspended in methanol and filtered to afford the desired product (2.6732 g, 80%). An additional 0.5768 g (17%) of product was obtained from the methanol filtrates. 1H NMR (300 MHz, DMSO, d6, TFA Shake) δ 7.86 (d, 1 H, Jm=2.7 Hz, ArH5), 7.55 (d, 1 H, Jm=2.7 Hz, ArH7), 7.32 (s, 1 H, C═CH), 3.94 (s, 3 H, OCH3); Mass Spec.: calc. for [C11H8BrNO4+H]+ Theor. m/z=298, 300; Obs.=298, 300.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into water
  3. customthe resulting solids were isolated by filtration
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b0afd574836543a9a94b3862700a3cfe
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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