Dimethylformamide → Methyl 3-methoxy-4-nitrobenzoate

HRID 1177347Notes

Reaction equation

HRID 1177347 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].[C:14]([O-])([O-])=O.[K+].[K+].CI.CN([CH:25]=[O:26])C>>[CH3:14][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:26][CH3:25])=[O:6]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoateYield 73.5%

Procedure

To a mixture of 3-hydroxy-4-nitrobenzoic acid (203 g, 1.109 mol) and K2CO3 (345 g, 2.496 mol) in DMF (3000 mL) was added drop wise CH3I (400 g, 2.817 mol) at ambient temperature. The mixture was stirred at ambient temperature for 13 h. TLC (EtOAc: Petroleum ether 1:4) indicated the reaction was complete. Most of the solvent was removed under reduced pressure and the residue was diluted with water (2 L). Then the mixture was extracted with EtOAc(2 L×3). The combined organic layers were washed with water (1 L×3), dried over Na2SO4 and concentrated under reduced pressure to yield the desired ester (172 g, 73.5%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.848-7.827 (d, 2H), 7.759 (s, 1H), 7.705-7.681 (d, 1H), 4.018 (s, 3H), 3.969 (s, 3H).

Workup

  1. customMost of the solvent was removed under reduced pressure
  2. additionthe residue was diluted with water (2 L)
  3. extractionThen the mixture was extracted with EtOAc(2 L×3)
  4. washThe combined organic layers were washed with water (1 L×3)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86c1fb3763394bd7955ada1836d6ceb9
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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