Triphenylphosphine → 6-Aminomethyl-2-chloro-nicotinic acid methyl ester

HRID 2076170Notes

Reaction equation

HRID 2076170 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]=[N+]=[N-])=[N:6][C:5]=1[Cl:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[N:6][C:5]=1[Cl:14]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 866377236-Azidomethyl-2-chloro-nicotinic acid methyl ester

Product 1

HCID 583245366-Aminomethyl-2-chloro-nicotinic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 6-azidomethyl-2-chloro-nicotinic acid methyl ester (4.75 g, 21 mmol) in THF (189 mL) and water (3.6 mL) was added triphenylphosphine (11 g, 42 mmol), the reaction mixture was heated at 45° C. for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue azeotroped with methanol. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0% to 10%, methanol in dichloromethane) to afford the title compound as a yellow solid. LCMS (method B): RT=2.65 min, [M+H]+=201.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue azeotroped with methanol

Sources & evidence

ORD record
ord-fb7cf00e7bed4b399d1fae7dd2ef4c6a
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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