Sulfuric Acid → 6,7-Dimethoxy-3-isoquinolinamine

HRID 1876026Notes

Reaction equation

HRID 1876026 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:6][NH:7][C:8](=[NH:16])[CH:9](OCC)OCC.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:21][O:20][C:19]1[CH:18]=[C:17]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH:6]=[N:7][C:8]([NH2:16])=[CH:9]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178471678HCID 178471678, compound

Product 1

HCID 233211636,7-Dimethoxy-3-isoquinolinamine

Procedure

To N-(3,4-dimethoxybenzyl)-2,2-diethoxyacetimidamide (541 mg, 1.825 mmol) was added sulfuric acid (0.95 mL, 1.825 mmol) was added. After cooling, the reaction was allowed to stand at ambient temperature overnight. It was added dropwise to ice, then the resulting solution was neutralized with conc. NaOH, and the aqueous phase was twice extracted with ethyl acetate. The combined ethyl acetate fractions were dried over magnesium sulfate. The drying agent was filtered off and the solvent evaporated. The residue was purified by column chromatography in 5% methanol/ethyl acetate, collecting the main component. Yield 105.7 mg brown solid (28%).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. additionIt was added dropwise to ice
  4. extractionthe aqueous phase was twice extracted with ethyl acetate
  5. dry with materialThe combined ethyl acetate fractions were dried over magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography in 5% methanol/ethyl acetate
  9. customcollecting the main component

Sources & evidence

ORD record
ord-a4913968c26f45ddbb3ed2629a6b6cf2
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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