Sodium Hydroxide → 1-Methylisoquinolin-6-amine

HRID 1173130Notes

Reaction equation

HRID 1173130 reaction equation
C(OC([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[N:12][CH:11]=[CH:10]2)=O)C.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[N:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 226741466-Ethoxycarbonylamino-1-methylisoquinoline

Product 1

HCID 226740791-Methylisoquinolin-6-amineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Ethoxycarbonylamino-1-methylisoquinoline (0.629 g, Production Example 32b) was dissolved in ethanol (20 ml), to which was then added an aqueous 8 N sodium hydroxide solution (6.8 ml), followed by heating under reflux for 1.5 hours. After cooling as it was to room temperature, an aqueous saturated ammonium chloride was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound (0.311 g, 72%) as pale yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling as it
  4. customwas to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-182de88d0e7c4a4a9416dc21e1e9f246
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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