4-Chloro-2-(chloromethyl)pyridine → 2-(Azidomethyl)-4-chloropyridine

HRID 1722565Notes

Reaction equation

HRID 1722565 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][N:4]=1.[N-:10]=[N+:11]=[N-:12].CC1C=CC=C2C=1C(C)=C(C)C(C)=N2>C(Cl)Cl>[N:10]([CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][N:4]=1)=[N+:11]=[N-:12]

Participants

4

Reactant 2

HCID 130529014-Chloro-2-(chloromethyl)pyridineHCID 20028922HCID 20028922, compound

Product 1

HCID 200288822-(Azidomethyl)-4-chloropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting material may be obtained as follows. Reaction of 2-chloromethyl-4-chloropyridine with excess tetramethylquinoline azide in CH2Cl2 at ambient temperature for 24 hours gave 2-azidomethyl-4-chlorpyridine. n.m.r. in CDCl3 :-4.5(s, 2H); 7.3(m, 2H); 8.5(d, 1H). Reduction of this compound in MeOH in the presence of 2 equivalents of acetic anhydride with Raneyl nickel at ambient temperature for 30 minutes gave, after purification by silica gel chromatography, 2-acetylaminomethyl-4-chloropyridine, n.m.r. in CDCl3 :-2.1(s, 3H); 4.56(d, 2H); 7.3(m, 2H); 8.48(d, 2H). Reaction of the compound with excess dimethyl sulphate for 30 minutes at 40° gave 2-acetylaminomethyl-4-chloro-1-methylpyridinium methyl sulphate, n.m.r. in solvent F:-2.0(s, 3H); 3.44(s, 3H9; 4.3(s, 3H); 4.7(s, 2H); 8.2(m, 2H); 9.04(d, 1H).

Workup

  1. customThe starting material may be obtained

Sources & evidence

ORD record
ord-c7519ca6c0e247aea065ce36f225198e
Source dataset
uspto-grants-1989_08
Patent number
US04855420

Reaction notes

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