Ammonium Chloride → HCID 22674100, compound

HRID 1173132Notes

Reaction equation

HRID 1173132 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

1-Chloro-6-ethoxycarbonylaminoisoquinoline (2.27 g, Production Example 41b) was dissolved in dimethyl sulfoxide (45 ml), to which was then added a 28% sodium methoxide solution (8.7 ml), followed by heating under stirring at 110° C. 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 (1.75 g, 84%) as a brown oil.

Workup

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

Sources & evidence

ORD record
ord-cd0878d6240e49c58af1ce2ce2939dff
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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