Sodium Hydroxide → 4-Amino-6-methoxyquinoline-3-carboxylic acid

HRID 2410146Notes

Reaction equation

HRID 2410146 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=[O:15].[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16644472Ethyl 4-amino-6-methoxyquinoline-3-carboxylate

Product 1

HCID 166444904-Amino-6-methoxyquinoline-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ethyl 4-amino-6-methoxyquinoline-3-carboxylate (Example Aa, 1.23 g, 5.0 mmol) in EtOH (20.0 mL) was added aqueous NaOH (2.0 N, 5.0 mL) at room temperature. The reaction mixture was then refluxed for 3 hr. The solution was then filtered and washed with water. The filtrate was cooled to 0° C. and neutralized carefully with 1 N HCl to pH 7. Most of the EtOH was removed under reduced pressure, and the precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as an off-white solid (1.01 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 3.89 (s, 3H), 7.40 (dd, J=2.8, 9.4 Hz, 1H), 7.73 (d, J=9.4 Hz, 1H), 7.77 (d, J=2.8 Hz, 1H), 8.77 (s, 1H). MS 219 (MH+).

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was then refluxed for 3 hr
  3. filtrationThe solution was then filtered
  4. washwashed with water
  5. customMost of the EtOH was removed under reduced pressure
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with cold water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-889b5b7cb7184a9ca1cece9ab69f77ce
Source dataset
uspto-grants-2014_08
Patent number
US08815956B2

Reaction notes

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