Methanol → HCID 178487707, compound

HRID 1188729Notes

Reaction equation

HRID 1188729 reaction equation
[Cl:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14]C)=[O:13])[CH:8]=[C:7]2[OH:16].CO.C1COCC1.[Li+].[OH-]>O>[Cl:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[C:7]2[OH:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178498513HCID 178498513, compound

Product 1

HCID 178487707HCID 178487707, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 8-chloro-4-hydroxy-7-methoxyquinoline-2-carboxylate (36.5 g, 0.145 mol) in a mixture of 1:1 of MeOH: THF (160 mL total) was added a solution of LiOH (30.5 g, 0.725 mol) in H2O (80 mL). The mixture was stirred at room temperature for an hour when LCMS analysis showed complete conversion to the carboxylic acid. The reaction was worked up by removal of the volatiles and adjusting the pH of the solution to 6 using aqueous 6N HCl. The resulted gummy residue was filtered and dried on the lypholizer for 2 days to provide 34.4 g (99.6%) of the product as a white solid. EI MS (m/z) 253.9 [M+H].

Workup

  1. customThe reaction was worked up by removal of the volatiles
  2. filtrationThe resulted gummy residue was filtered
  3. customdried on the lypholizer for 2 days

Sources & evidence

ORD record
ord-6b1002fdbdde4a5e82fbec1297404ee0
Source dataset
uspto-grants-2014_03
Patent number
US08674088B2

Reaction notes

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