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

HRID 993282Notes

Reaction equation

HRID 993282 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-f111f037c575485caa3fcd38c590df04
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

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