Ammonium Chloride → HCID 22674100, compound

HRID 1005689Notes

Reaction equation

HRID 1005689 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([O:15][CH2:16]C)=[O:14])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:18][O-:19].[Na+].[Cl-].[NH4+]>CS(C)=O>[CH3:18][O:19][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 22674084HCID 22674084, compound

Product 1

HCID 22674100HCID 22674100, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

In dimethyl sulfoxide (45 ml) was dissolved 2.27 g of 1-chloro-6-ethoxycarbonylaminoisoquinoline (Preparation Example 41). To the mixture was added 28% sodium methoxide solution (8.7 ml), followed by heating under stirring at 110° C. for 1.5 hours. After cooling to room temperature as it was, an aqueous saturated ammonium chloride was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (1.75 g, 84%) as a brown oil.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling to room temperature as it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9c034d9c65f646a9961324b873690023
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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