Hydrochloric Acid → HCID 22175746, compound

HRID 1797505Notes

Reaction equation

HRID 1797505 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:6]([C:17]([O:19]CC)=[O:18])=[C:5]2[O:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+].O.Cl>O1CCCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]1[CH2:15][CH2:16]1)[C:6]([C:17]([OH:19])=[O:18])=[C:5]2[O:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22176064Ethyl 6-bromo-4-butoxy-2-cyclopropylmethyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate

Product 1

HCID 22175746HCID 22175746, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-bromo-4-butoxy-2-cyclopropylmethyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (7.18 g, 17 mmol) in tetrahydrofuran (20 mL) and ethanol (20 mL) was added an aqueous solution (10 mL) of sodium hydroxide (2.04 g, 51 mmol). The obtained mixture was refluxed under heating for 12 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 was recrystallized from ethyl acetate-diisopropyl ether to give 6-bromo-4-butoxy-2-cyclopropylmethyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylic acid (6.41 g, 95.7%) as crystals.

Workup

  1. temperatureThe obtained mixture was refluxed
  2. temperatureunder heating for 12 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crystals was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-938852234caf4f1ba53a8daf1f6b8cd1
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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