Trifluoroacetic acid → 1-Isoquinolinamine

HRID 1878641Notes

Reaction equation

HRID 1878641 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=CC=1.COC1C=CC(CNC2C3C(=CC=C(N(C)C)C=3)C=C(C3C=CC=C(OC)C=3)N=2)=CC=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 19771021HCID 19771021, compoundHCID 692989333-(3-Methoxyphenyl)-N1-[(4-methoxyphenyl)methyl]-N7,N7-dimethyl-1,7-isoquinolinediamine

Product 1

HCID 737421-IsoquinolinamineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of N1-(4-methoxy benzyl)-isoquinolinamine compound III (300 mg, 0.73 mmol) and trifluoroacetic acid (5 mL) in methylene chloride (5 mL) was refluxed for 2 days. A solution of NaHCO3 was added and the reaction mixture was extracted with methylene chloride. The combined organic extracts were washed with water, dried, and concentrated. The residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (1:1) to afford 1-amino isoquinoline (151 mg, 71%). The 1-amino compound was dissolved in acetone (5 mL) and 5 drops of concentrated HCl was added. The hydrochloride salt was filtered and filter cake was washed with acetone. After drying, 120 mg of 1-amino isoquinoline hydrochloride was obtained (Compound 13, 50%). 1H NMR (300 MHz, DMSO-d6) δ: 13.57 (s, 1H), 9.37 (s, 2H), 7.79 (d, 1H), 7.55-7.39 (m, 6H), 7.02 (m, 1H), 3.87 (s, 3H), 3.06 (s, 6H).

Workup

  1. temperaturewas refluxed for 2 days
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b7c55404060c487c868142749e1b6cb6
Source dataset
uspto-grants-2012_11
Patent number
US08314123B2

Reaction notes

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