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

HRID 1092831Notes

Reaction equation

HRID 1092831 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. Recrystallisation 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-8531eb70135b4aed9ec05e261eb4be5e
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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