Water → Quinolin-3-ylmethanamine

HRID 1271776Notes

Reaction equation

HRID 1271776 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=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]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18400510HCID 18400510, compound

Product 1

HCID 6483745Quinolin-3-ylmethanamineYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3(azidomethyl)quinoline (250 mg, 1.36 mmol) and triphenylphosphine (880 mg, 3.36 mmol, 2.5 equiv) were dissolved in 10 mL THF. The reaction mixture was treated with 0.5 mL of H2O and refluxed for 6 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 (104 mg) as a brown oil. MS(CI) m/e 159 (M+H)+.

Workup

  1. temperaturerefluxed for 6 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-dd52068fedcd4c14a227c6f2b6d00c1d
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

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