Triphenylphosphine → Methyl 4-(aminomethyl)-2-chlorobenzoate

HRID 2355273Notes

Reaction equation

HRID 2355273 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:34])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]=[N+]=[N-])=[CH:25][C:24]=1[Cl:33]>O1CCCC1.O>[CH3:20][O:21][C:22](=[O:34])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][C:24]=1[Cl:33]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 57461226Methyl 4-(azidomethyl)-2-chlorobenzoate

Product 1

HCID 55263540Methyl 4-(aminomethyl)-2-chlorobenzoateYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add triphenylphosphine (30.3 g, 115 mmol) to crude 4-azidomethyl-2-chloro-benzoic acid methyl ester (5.8 g, 25.7 mmol) in tetrahydrofuran (152 mL) and water (4.6 mL). Stir the reaction mixture at room temperature overnight. Concentrate the reaction mixture and partition the residue between 1N hydrochloric acid and ethyl acetate. Separate the organic layer and wash the organic layer with water. Combine the aqueous layers, wash with ethyl acetate, and then neutralize with 1N sodium hydroxide. Extract the resulting aqueous mixture with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the crude title compound (2.2 g, 11.0 mmol). MS (m/z): 200 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture
  2. custompartition the residue between 1N hydrochloric acid and ethyl acetate
  3. customSeparate the organic layer
  4. washwash the organic layer with water
  5. washwash with ethyl acetate
  6. extractionExtract the resulting aqueous mixture with ethyl acetate (3×)
  7. washCombine the organic layers, wash with brine
  8. dry with materialdry over sodium sulfate
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-4aa2fca64a0c48dcb5473ac3559a96cf
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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