Triphenylphosphine → HCID 10867424, compound

HRID 1370322Notes

Reaction equation

HRID 1370322 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C:23]1[C:32]2[C:27](=[C:28]([O:35][CH3:36])[CH:29]=[CH:30][C:31]=2[O:33][CH3:34])[N:26]=[CH:25][CH:24]=1)=[N+]=[N-]>C1COCC1.O>[NH2:20][C:23]1[C:32]2[C:27](=[C:28]([O:35][CH3:36])[CH:29]=[CH:30][C:31]=2[O:33][CH3:34])[N:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11791017HCID 11791017, compound

Product 1

HCID 10867424HCID 10867424, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

12 g (45.8 mmol) of triphenylphosphine are added in a single portion to a solution of 8.7 g (37.8 mmol) of 4-azido-5,8-dimethoxyquinoline in a THF/H2O mixture (110 mL/110 mL). The reaction medium is stirred at ambient temperature for 2 hours and then concentrated on a rotary evaporator. The residue is acidified with 200 mL of 1N HCl and extracted with ether (3 times 500 mL). The aqueous phase is then basified with 250 mL of 1N NaOH and re-extracted with CHCl3 (3 times 250 mL). After drying over MgSO4 and evaporating off the solvent on a rotary evaporator, the expected amine is obtained quantitatively in the form of brown powder, which decomposes before melting.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. extractionextracted with ether (3 times 500 mL)
  3. extractionre-extracted with CHCl3 (3 times 250 mL)
  4. dry with materialAfter drying over MgSO4
  5. customevaporating off the solvent
  6. customon a rotary evaporator

Sources & evidence

ORD record
ord-f11fd9f80d8f419986f0ec0605c02533
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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