Methanol → HCID 178487707, compound

HRID 1053485Notes

Reaction equation

HRID 1053485 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.[Li+].[OH-]>C1COCC1>[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

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 178498513HCID 178498513, compound

Product 1

HCID 178487707HCID 178487707, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 8-chloro-4-hydroxy-7-methoxyquinoline-2-carboxylate 214 (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 H20 (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 lyophilizer for 2 days to provide 34.4 g (99.6%) of compound 215 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 lyophilizer for 2 days

Sources & evidence

ORD record
ord-ad9e8f5ea3424dc6b98c6d428e213c57
Source dataset
uspto-grants-2016_07
Patent number
US09393256B2

Reaction notes

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