Triphenylphosphine → N-methylquinolin-5-amine

HRID 1819452Notes

Reaction equation

HRID 1819452 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C[C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[N:29]2)=[N+]=[N-].[OH-].[Na+].[OH-].[NH4+:37]>C1COCC1.C(OCC)(=O)C>[N:37]1[C:24]2[C:25](=[C:30]([NH:29][CH3:28])[CH:31]=[CH:32][CH:33]=2)[CH:26]=[CH:27][CH:1]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 578855385-Azidomethyl-quinoline

Product 1

HCID 348010N-methylquinolin-5-amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenylphosphine (172 mg, 0.65 mmol) was added to the solution of 5-azidomethyl-quinoline (109 mg, 0.59 mmol) in THF (3 mL) at 0° C. After 5 min of stirring, the reaction mixture was warmed to room temperature and stirred at that temperature 16 h. The reaction mixture was diluted with ammonium hydroxide (0.55 mL) and stirred for 3 h. The mixture was then treated with 2M NaOH (0.8 mL) and stirred for another 1 h. The solution was diluted with ethyl acetate and the organic phase was separated, dried over Na2SO4, concentrated. The resulting residue was purified by silica gel prep TLC using 10:1:0.3 CH2Cl2:MeOH:Et3N as an eluant to afford 105 mg of quinolin-5-yl-methylamine as a colorless solid.

Workup

  1. stirringstirred at that temperature 16 h
  2. stirringstirred for 3 h
  3. stirringstirred for another 1 h
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-454c5ded389f432480885cda0ed404b3
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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