Hydrochloric Acid → HCID 70028747, compound

HRID 986997Notes

Reaction equation

HRID 986997 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([C:12]([O:14]C)=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.Cl>O>[ClH:1].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22646520Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

Product 1

HCID 70028747HCID 70028747, compoundYield 171.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 4-chloro-7-methoxyquinoline-6-carboxylate (3 g) and concentrated aqueous hydrochloric acid (36%; 75 ml) was stirred and heated to 90° C. for 45 minutes. The mixture was allowed to cool to ambient temperature, poured into water (150 ml) and washed with methylene chloride. Evaporation of the aqueous phase gave 4-chloro-7-methoxyquinoline-6-carboxylic acid hydrochloride (2.8 g); NMR Spectrum: (DMSOd6) 3.98 (s, 3H), 7.6 (s, 1H), 7.7 (d, 1H), 8.4 (s, 1H), 8.86 (d, 1H).

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with methylene chloride
  3. customEvaporation of the aqueous phase

Sources & evidence

ORD record
ord-2a9abe78abbe4804a9675cffb2afa472
Source dataset
uspto-grants-2003_10
Patent number
US06630489B1

Reaction notes

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