Hydrochloric Acid → HCID 22175425, compound

HRID 1797472Notes

Reaction equation

HRID 1797472 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([C:14]([O:16]CC)=[O:15])=[C:5]2[O:19][CH3:20].[OH-].[Na+].O.Cl>O1CCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([C:14]([OH:16])=[O:15])=[C:5]2[O:19][CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22176226HCID 22176226, compound

Product 1

HCID 22175425HCID 22175425, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 6-chloro-4-methoxy-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (1.03 g, 3.5 mmol) in tetrahydrofuran (10 ml) and ethanol (10 ml) was added 1N sodium hydroxide (5 ml). The obtained mixture was refluxed under stirring at 50° C. for 3 h. The reaction mixture was poured into water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate diethyl ether to give 6-chloro-4-methoxy-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylic acid (0.72 g, 77.4%) as crystals.

Workup

  1. temperatureThe obtained mixture was refluxed
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crystals were recrystallized from ethyl acetate diethyl ether

Sources & evidence

ORD record
ord-0c4dcf63d88b44c3bf036e629c7ac586
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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