1-(3,4,5-Trimethoxybenzyl)amino-6-fluoro-isoquinoline → 6-Fluoroisoquinolin-1-amine

HRID 2244066Notes

Reaction equation

HRID 2244066 reaction equation
COC1C=C(C=C(OC)C=1OC)C[NH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1>C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([F:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 1

HCID 675297941-(3,4,5-Trimethoxybenzyl)amino-6-fluoro-isoquinoline

Product 1

HCID 250594376-Fluoroisoquinolin-1-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(3,4,5-trimethoxybenzyl)amino-6-fluoro-isoquinoline (1.26 g, 3.68 mmol) in TFA (30 mL) is refluxed for 16 h. The solvent is evaporated under reduced pressure. Anhydrous MeOH (30 mL) is added to the residue. Solid K2CO3 is slowly added until pH>8. The suspension is filtered through a pad of Celite, and the solvent is evaporated under reduced pressure. The residue is dissolved in CH2Cl2 and filtered through a pad of Celite. The filter cake is rinsed with CH2Cl2, and the solvent is evaporated under reduced pressure. The residue is dried under vacuum to afford 0.41 g (69%) of 1-amino-6-fluoro-isoquinoline. LC/MS m/z=163 [M+H]+.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. additionAnhydrous MeOH (30 mL) is added to the residue
  3. additionSolid K2CO3 is slowly added until pH>8
  4. filtrationThe suspension is filtered through a pad of Celite
  5. customthe solvent is evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in CH2Cl2
  7. filtrationfiltered through a pad of Celite
  8. washThe filter cake is rinsed with CH2Cl2
  9. customthe solvent is evaporated under reduced pressure
  10. customThe residue is dried under vacuum

Sources & evidence

ORD record
ord-46f5c3ea12e94d8684033031ea675dcb
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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