Benzenemethanamine, 3,4-dimethyl- → HCID 66724741, compound

HRID 1876014Notes

Reaction equation

HRID 1876014 reaction equation
C(O[CH:4](OCC)[C:5](=[NH:8])OC)C.[CH3:12][C:13]1[CH:14]=[C:15]([CH2:20][NH2:21])[CH:16]=[CH:17][C:18]=1[CH3:19]>CO>[CH3:19][C:18]1[CH:17]=[C:16]2[C:4](=[CH:12][C:13]=1[CH3:14])[CH:5]=[N:8][C:20]([NH2:21])=[CH:15]2.[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:4]2[C:14]=1[CH:15]=[C:20]([NH2:21])[N:8]=[CH:5]2

Participants

5

Reactant 2

HCID 66888Benzenemethanamine, 3,4-dimethyl-HCID 17874536Methyl 2,2-diethoxyethanecarboximidate

Product 2

HCID 59286677HCID 59286677, compoundHCID 66724741HCID 66724741, compoundYield 219.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 2,2-diethoxyacetimidate (1.50 g, 9.32 mmol) in methanol (4.9 mL) was added (3,4-dimethylphenyl)methanamine (1.20 g, 8.88 mmol) dropwise at ambient temperature. The reaction flask was then placed into a preheated oil-bath and stirred at 70° C. for 16 h; after which time, the flask was removed from the oil-bath and allowed to cool to ambient temperature. The volatiles were removed under reduced pressure and the crude material was added dropwise to sulfuric acid (19.7 mL) at ambient temperature. The reaction mixture was stirred for 72 h, then the flask was placed into an ice-water bath, diluted with water (50 mL), and slowly neutralized to pH=10 with sodium hydroxide (10 N). As the reaction mixture became basic, an orange precipitate formed. This precipitate was filtered, washed with water, and dried to afford a mixture (2:1) of 6,7-dimethylisoquinolin-3-amine and 5,6-dimethylisoquinolin-3-amine (1.68 g, 9.75 mmol, >100%). MS (LC/MS) R.T.=0.32; [M+H]+=173.13.

Workup

  1. customThe reaction flask was then placed into a preheated oil-bath
  2. customafter which time, the flask was removed from the oil-bath
  3. temperatureto cool to ambient temperature
  4. customThe volatiles were removed under reduced pressure
  5. additionthe crude material was added dropwise to sulfuric acid (19.7 mL) at ambient temperature
  6. stirringThe reaction mixture was stirred for 72 h
  7. customthe flask was placed into an ice-water bath
  8. additiondiluted with water (50 mL)
  9. customan orange precipitate formed
  10. filtrationThis precipitate was filtered
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-17ee065cff50481fb4dfedd70261e708
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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