Hydrochloric Acid → 7-Ethoxyquinoline-8-carboxylic acid

HRID 2175944Notes

Reaction equation

HRID 2175944 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([C:14]([O:16]CC)=[O:15])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH3:2].O[Li].O.CO.Cl>C1COCC1.O>[CH2:1]([O:3][C:4]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrate3×HCID 90411629Ethyl 7-ethoxyquinoline-8-carboxylate

Product 1

HCID 904121657-Ethoxyquinoline-8-carboxylic acidYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
67 °C

Procedure

To the title compound of Step C (1.3 g, 5.4 mmol) in THF (22 mL) and H2O (11 mL) was added LiOH hydrate (675 mg, 16.5 mmol) and MeOH. The mixture was heated at 67° C. for 12 h. Additional LiOH hydrate (675 mg, 16.5 mmol) was added and the heating was continued at 70° C. for 1 days. Additional LiOH hydrate (1.4 g, 33 mmol) was added and the heating was continued at 75° C. for 1 day. The reaction was allowed to cool to rt, acidified to pH=3 with 1N HCl (aq) and concentrated. Purification via prep HPLC gave the title compound (1 g, 84%). MS (ESI) mass calcd. for C12H11NO3, 217.1; m/z found 218.0 [M+H]+.

Workup

  1. waitthe heating was continued at 75° C. for 1 day
  2. temperatureto cool to rt
  3. concentrationconcentrated
  4. customPurification via prep HPLC

Sources & evidence

ORD record
ord-fa18f22ab9114721b34b47a1cec34cf5
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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