Hydrochloric Acid → HCID 22175363, compound

HRID 1797586Notes

Reaction equation

HRID 1797586 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24]([O:26]CC)=[O:25])=[C:12]2[O:29][CH2:30][CH2:31][CH2:32][C:33]([F:36])([F:35])[F:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24]([OH:26])=[O:25])=[C:12]2[O:29][CH2:30][CH2:31][CH2:32][C:33]([F:34])([F:35])[F:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22175233HCID 22175233, compound

Product 1

HCID 22175363HCID 22175363, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-benzyloxy-2-isobutyl-1-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydro-3-isoquinolinecarboxylate (6.57 g, 13 mmol) in ethanol (50 mL) was added an aqueous solution (20 mL) of sodium hydroxide (2.08 g, 52 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 were recrystallized from ethyl acetate-n-hexane to give 6-benzyloxy-2-isobutyl-1-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydro-3-isoquinolinecarboxylic acid (4.89 g, 78.7%) 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 were recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-18ec0bc333d0400c8bccf88041ec5e25
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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