Water → 6-(Aminomethyl)quinoline

HRID 1271777Notes

Reaction equation

HRID 1271777 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 22131439HCID 22131439, compound

Product 1

HCID 15143846-(Aminomethyl)quinolineYield 25.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(azidomethyl)quinoline (320 mg) and triphenylphosphine (880 mg) were dissolved in 7 mL THF. The reaction mixture was treated with 0.5 mL of H2O and refluxed for 7 hours. The reaction mixture was cooled and partitioned between Et2O and 1N HCl. The aqueous portion was then treated with 1N NaOH until basic and extracted into EtOAc. The organic portion was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (70 mg) as a brown oil. MS(CI) m/e 159 (M+H)+.

Workup

  1. temperaturerefluxed for 7 hours
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between Et2O and 1N HCl
  4. additionThe aqueous portion was then treated with 1N NaOH until basic and
  5. extractionextracted into EtOAc
  6. dry with materialThe organic portion was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfd1f414199346cd93979b510f3bcb57
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

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