Hydrochloric Acid → HCID 22945886, compound

HRID 1363668Notes

Reaction equation

HRID 1363668 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[Cl:12])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+].Cl>C1COCC1.O.O>[Cl:12][C:6]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][NH2:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 89225429HCID 89225429, compound

Product 1

HCID 22945886HCID 22945886, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

1-Azidomethyl-2-chloro-3-methyl-benzene (2.99 g, 16.50 mmol) was dissolved in THF:H2O (3:1), triphenyl phosphine (4.40 g, 16.78 mmol) was added, followed by KOH (923 mg, 16.45 mmol) and the resulting mixture was stirred for 14 hours. The reaction mixture was then diluted with H2O, slowly acidified with HCl and the resulting aqueous layer was washed with Et2O (3×50 mL). The aqueous layer was then basified with NaOH (pH 14), extracted with Et2O (3×100 mL). The combined organic phases were washed with H2O (1×50 mL) and brine (1×50 mL), then dried over K2CO3 and concentrated to give the title amine.

Workup

  1. washthe resulting aqueous layer was washed with Et2O (3×50 mL)
  2. extractionextracted with Et2O (3×100 mL)
  3. washThe combined organic phases were washed with H2O (1×50 mL) and brine (1×50 mL)
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab0e4dd1e8b34ed9a18133f4769463bd
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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