Sodium Hydroxide → 6-Aminoquinoline-5-carboxylic acid

HRID 245645Notes

Reaction equation

HRID 245645 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[CH:13][C:14]=1[NH2:15])=[O:4].[OH-].[Na+]>O1CCOCC1.CO>[NH2:15][C:14]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 45089602Methyl 6-aminoquinoline-5-carboxylate

Product 1

HCID 205642906-Aminoquinoline-5-carboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 540 mg (2.19 mmol) of the above 6-amino-quinoline-5-carboxylic acid methyl ester in 10.8 mL of dioxane and 0.54 mL of methanol is added 5.48 mL (5.48 mmol) of an aqueous solution of NaOH 1N. The reaction is stirred 24 hours at ambient temperature. Then the solvents are evaporated in vacuo and the residue is suspended in a minimum of water and precipitated at pH 6 by addition of concentrated HCl. After filtration and washing with a minimum of water the solid obtained is dried on high vacuum pump to give 245 mg (60%) of a yellowish solid; LC/MS:189/190 (M+H)+.

Workup

  1. customThen the solvents are evaporated in vacuo
  2. customprecipitated at pH 6 by addition of concentrated HCl
  3. filtrationAfter filtration
  4. washwashing with a minimum of water the solid
  5. customobtained
  6. customis dried on high vacuum pump

Sources & evidence

ORD record
ord-bc97cc84b1124a5b91c68260ea187eec
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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