Dimethylformamide → Methyl 5-methoxy-2-nitrobenzoate

HRID 1672322Notes

Reaction equation

HRID 1672322 reaction equation
O[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)C(O)=O.[C:14](=[O:17])([O-])[O-:15].[K+].[K+].[CH3:20]I.CN([CH:25]=[O:26])C>O>[CH3:20][O:15][C:14](=[O:17])[C:4]1[CH:3]=[C:2]([O:26][CH3:25])[CH:10]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118825-Hydroxy-2-nitrobenzoic acid

Product 1

HCID 12719167Methyl 5-methoxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

20 g (0.109 mol) of 5-hydroxy-2-nitro-benzoic acid (Example 44a) and 32.7 g (0.247 mol) potassium carbonate are stirred for 15 min in 163 ml of DMF. 23.8 ml (0.383 mol) of methyl iodide are added and the reaction mixture is stirred for 4 h at 75° C. The cold reaction mixture is diluted with water and is extracted with ether. After drying the organic phase with sodium sulfate, the solvent is evaporated to dryness. The residue, a yellow oil, is used in the next step without further purification. HPLC: tret=1.07 min (Grad 1); NMR (DMSO-d6): 8.15/d (1H), 7.29/s (1H), 7.26/d×d (1H), 3.92/s (3H) and 3.85/s (3H).

Workup

  1. customThe cold reaction mixture
  2. extractionis extracted with ether
  3. dry with materialAfter drying the organic phase with sodium sulfate
  4. customthe solvent is evaporated to dryness
  5. customThe residue, a yellow oil, is used in the next step without further purification
  6. customtret=1.07 min (Grad 1)

Sources & evidence

ORD record
ord-8852b86ea5554b2ba989a16cae449eff
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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