Toluene → Methyl 4-chloro-6-(chloromethyl)pyridine-2-carboxylate

HRID 2356622Notes

Reaction equation

HRID 2356622 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.S(Cl)([Cl:16])=O.C1(C)C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:16])[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 14083517Methyl 4-chloro-6-(hydroxymethyl)pyridine-2-carboxylate

Product 1

HCID 68456565Methyl 4-chloro-6-(chloromethyl)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-chloro-6-(hydroxymethyl)-2-pyridinecarboxylate (166 mg, Ref: Kittika et al., Tetrahedron, 44 (10), 2821, (1988)) in dry dichloromethane (3 ml) was added thionyl chloride (66 μl). The solution was stirred for 40 minutes. LC/MS indication reaction completion. Solvent was removed u.r.p. (under reduced pressure) to give a white solid. Toluene (˜2 ml) added then removed u.r.p. The residue was dried in vacuo to give a white solid. (175 mg, 97%). LC/MS [MH+]=220/222, Rt=2.51 min. Title compound obtained as the free base.

Workup

  1. customLC/MS indication reaction completion
  2. customSolvent was removed u.r.p
  3. custom(under reduced pressure) to give a white solid
  4. customthen removed u.r.p
  5. customThe residue was dried in vacuo
  6. customto give a white solid

Sources & evidence

ORD record
ord-e23950b542e54805a0240b04517cfd5e
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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