Trifluoroacetic acid → 6-Nitroisoquinolin-1-amine

HRID 2104967Notes

Reaction equation

HRID 2104967 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=2)[C:7]1=[NH:19].C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1>[N+:16]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7]([NH2:19])=[N:6][CH:15]=[CH:14]2)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 208016702-[(2,4-Dimethoxyphenyl)methyl]-6-nitroisoquinolin-1(2H)-imine

Product 1

HCID 219199846-Nitroisoquinolin-1-amineYield 90.6%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(2,4-dimethoxybenzyl)-6-nitroisoquinolin-1(2H)-imine (11.9 g, 35 mmol) in anisole (24 mL) was added TFA (24 mL). The reaction mixture was stirred at 90° C. for 6 h and the solvent was removed under reduced pressure. The residue was suspended in MeOH (30 mL) and then treated with NaOH (1.0 N, 38 mL). The mixture was stirred at rt for 10 min and pH was checked to be 9-10. The precipitate was collected by filtration and washed with water to afford 6-nitroisoquinolin-1-amine (6.0 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.20 (d, J=5.72 1 H) 7.36 (s, 2 H) 7.95 (d, J=5.72 Hz, 1 H) 8.15 (dd, J=9.24, 2.64 Hz, 1 H) 8.43 (d, J=9.24 Hz, 1 H) 8.67 (d, J=2.64 Hz, 1 H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additiontreated with NaOH (1.0 N, 38 mL)
  3. stirringThe mixture was stirred at rt for 10 min
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-dbe16e243f974ca1b418e015fb316bc4
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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