Acetic Acid → HCID 59323166, compound

HRID 2390048Notes

Reaction equation

HRID 2390048 reaction equation
[CH2:1]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[CH3:15])[CH2:7][N:6]1C(OC)=O)[CH:2]([CH3:4])[CH3:3].C(O)(=O)C.O.[OH-].[Na+]>Cl>[CH2:1]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[CH3:15])[CH2:7][NH:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59323169HCID 59323169, compound

Product 1

HCID 59323166HCID 59323166, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 20 mg of methyl 3-isobutyl-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate in hydrochloric acid (0.8 mL)-acetic acid (0.3 mL) was reacted at 90° C. for 48 hours. Under ice-cooling, the reaction liquid was diluted by addition of water, alkalized with 5 N sodium hydroxide, and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by PLC (chloroform:ammonia saturated methanol=20:1) to obtain 13 mg (yield 84%) of a title compound as a light yellow oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. customthe reaction liquid
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by PLC (chloroform:ammonia saturated methanol=20:1)

Sources & evidence

ORD record
ord-8412749dd9324be7ae17a66a94acc0df
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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