Sodium Hydroxide → 1-Methylisoquinolin-6-amine

HRID 1005687Notes

Reaction equation

HRID 1005687 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

In ethanol (20 ml) was dissolved 0.629 g of 6-ethoxycarbonylamino-1-methylisoquinoline (Preparation Example 32), and 8 N sodium hydroxide aqueous 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, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and 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. extractionby extracting 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-c6d1b7d673704c1aba24c2f6203a9b2d
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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