Trifluoroacetic acid → N-METHYLQUINOLIN-3-AMINE

HRID 1944515Notes

Reaction equation

HRID 1944515 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[CH:2]=1.F[C:13](F)(F)C(O)=O>C(OCC)(OCC)OCC>[CH3:13][NH:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 113753-Aminoquinoline

Product 1

HCID 12548159N-METHYLQUINOLIN-3-AMINE

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

A solution of quinolin-3-ylamine (5.2 g, 36.1 mmol) and trifluoroacetic acid (catalytic) in triethyl orthoformate (30 mL) was heated at reflux for 6 hours. The solvent was evaporated in vacuo, and the residue was dissolved in ethanol (50 mL). Sodium borohydride tablets (2.5 g, 0.203 mol) was added to the solution, and the resultant mixture was stirred at room temperature for 2.5 days. The mixture was partitioned between water and dichloromethane. The organic layer was separated, washed with water and dried over sodium sulfate. The solvent was evaporated in vacuo, to give the product, 5.35 g (94%), an oil, which crystallized on standing. MS: m/z 159 (MH+). 1H NMR (CDCl3): 2.90 (d, 3 H), 4.15 (br s, 1 H), 6.97 (d, 1 H), 7.36-7.47 (m, 2 H), 7.55-7.65 (m, 1 H), 7.91-7.96 (m, 1 H) and 8.42 (d, 1 H).

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ethanol (50 mL)
  4. additionwas added to the solution
  5. customThe mixture was partitioned between water and dichloromethane
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was evaporated in vacuo
  10. customto give the product, 5.35 g (94%)
  11. customan oil, which crystallized

Sources & evidence

ORD record
ord-d59f7abfc7e8409486f5182547db66fd
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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