Methyl 6-chloro-5-nitronicotinate → methyl 6-methoxy-5-nitronicotinate

HRID 1825391Notes

Reaction equation

HRID 1825391 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1>CO>[CH3:1][O:2][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 2746880methyl 6-methoxy-5-nitronicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide in methanol (82.65 mL of a 1 M solution) is added slowly to a stirred solution of methyl 6-chloro-5-nitronicotinate (17 g) in anhydrous methanol (250 mL) and the mixture stirred for 8 hours. The mixture is concentrated, the residue treated with water and then extracted into ethyl acetate. The extracts are washed with water, treated with decolourising charcoal and dried (MgSO4). Concentration afforded methyl 6-methoxy-5-nitronicotinate (9.8 g) as an orange solid. Recrstallisation from cyclohexane afforded white needles, m.p. 118–9° C.

Workup

  1. concentrationThe mixture is concentrated
  2. additionthe residue treated with water
  3. extractionextracted into ethyl acetate
  4. washThe extracts are washed with water
  5. additiontreated with decolourising charcoal
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration

Sources & evidence

ORD record
ord-e500c9c8369c4b2f8f7d529e6d8cc23d
Source dataset
uspto-grants-2006_05
Patent number
US07045660B2

Reaction notes

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