Hydrochloric Acid → 1093651-77-4

HRID 1876281Notes

Reaction equation

HRID 1876281 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([Cl:34])[CH:32]=2)[CH:27]=[CH:26][CH:25]=1)=[N+]=[N-].Cl.C([O-])(O)=O.[Na+]>C1COCC1.O>[ClH:34].[Cl:34][C:31]1[CH:32]=[C:33]2[C:28]([CH:27]=[CH:26][CH:25]=[C:24]2[CH2:23][NH2:20])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 86646305HCID 86646305, compound

Product 1

HCID 687009031093651-77-4

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.24 g of Triphenylphosphine and 410 μl of H2O are added to 998 mg of 1-azidomethyl-7-chloro-naphthalene in 20 ml of THF. The mixture obtained is stirred at 50° for 5 hours and solvent is evaporated. The residue obtained is acidified with aq. 1N HCl solution and extracted with EtOAc. The aq. phase obtained is basified with aq. 10% NaHCO3 solution and extracted with EtOAc. The organic phase obtained is dried and solvent is evaporated. The title compound is obtained as the free amine compound and converted to the hydrochloride salt by addition of 4M HCl solution in dioxane. Solvent is evaporated and the residue obtained is stirred with ether, the mixture obtained is filtered and the filtrate obtained is dried to yield the title compound.

Workup

  1. customThe mixture obtained
  2. customsolvent is evaporated
  3. customThe residue obtained
  4. extractionextracted with EtOAc
  5. customThe aq. phase obtained
  6. extractionextracted with EtOAc
  7. customThe organic phase obtained
  8. customis dried
  9. customsolvent is evaporated

Sources & evidence

ORD record
ord-bfbd51f075af45caa085ada2db1cd7c2
Source dataset
uspto-grants-2012_11
Patent number
US08309596B2

Reaction notes

Loading…