Trifluoroacetic acid → 6-Nitroisoquinolin-1-amine

HRID 735492Notes

Reaction equation

HRID 735492 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.C([O-])(O)=O.[Na+]>C1(OC)C=CC=CC=1.O>[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

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 208016702-[(2,4-Dimethoxyphenyl)methyl]-6-nitroisoquinolin-1(2H)-imine

Product 1

HCID 219199846-Nitroisoquinolin-1-amineYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7519AnisoleSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of Intermediate 1B (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 (50 mL) and then treated with NaHCO3 (3.3 g, 39 mmol) in water (200 mL). The mixture was stirred at rt for 15 min and the pH was checked to be 9-10. The precipitate was collected by filtration and washed with water to afford Intermediate 1C (6.0 g, 91%). 1H NMR (400 MHz, DMSO-d6) δ 7.20 (d, J=5.7 Hz, 1H), 7.36 (s, 2H), 7.95 (d, J=5.7 Hz, 1H), 8.15 (dd, J=9.2, 2.6 Hz, 1H), 8.43 (d, J=9.2 Hz, 1H), 8.67 (d, J=2.6 Hz, 1H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. stirringThe mixture was stirred at rt for 15 min
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-7b0bd1c97ad44381a888b43b16dbd6b0
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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