Sodium Hydroxide → 6-Amino-7-methyl-quinoline-5-carboxylic acid

HRID 245651Notes

Reaction equation

HRID 245651 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]=[C:13]([CH3:16])[C:14]=1[NH2:15])=[O:4].[OH-].[Na+]>O1CCOCC1.CO>[NH2:15][C:14]1[C:13]([CH3:16])=[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 579901536-Amino-7-methyl-quinoline-5-carboxylic acid methyl ester

Product 1

HCID 579901086-Amino-7-methyl-quinoline-5-carboxylic acidYield 54.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 550 mg (2.54 mmol) of 6-amino-7-methyl-quinoline-5-carboxylic acid methyl ester in 11 mL of dioxane and 0.5 mL of methanol, is added 6.4 mL (6.4 mmol) of an aqueous solution of NaOH 1N. The mixture is stirred at ambient temperature for 16 hours. The solvents are evaporated and water is added to the residue. The product is precipitated at pH 6 by addition of concentrated HCl, filtrated, washed with a minimum of water and dried on high vacuum pump. The yellow crude solid (282 mg) obtained is used directly in the next step; LC/MS: 203/204 (M+H)+.

Workup

  1. customThe solvents are evaporated
  2. additionwater is added to the residue
  3. customThe product is precipitated at pH 6 by addition of concentrated HCl
  4. filtrationfiltrated
  5. washwashed with a minimum of water
  6. customdried on high vacuum pump

Sources & evidence

ORD record
ord-fda2c7b81488472fb562c1f93f27bcf4
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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