Oxalyl chloride → Methyl 3,5-dimethoxy-4-hydroxy-2-nitrobenzoate

HRID 1830960Notes

Reaction equation

HRID 1830960 reaction equation
[C:1](Cl)(=O)C(Cl)=O.C([O:10][C:11]1[C:19]([O:20][CH3:21])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([N+:22]([O-:24])=[O:23])[C:12]=1[O:25][CH3:26])(=O)C>CN(C=O)C.C1COCC1>[CH3:26][O:25][C:12]1[C:13]([N+:22]([O-:24])=[O:23])=[C:14]([CH:18]=[C:19]([O:20][CH3:21])[C:11]=1[OH:10])[C:15]([O:17][CH3:1])=[O:16]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 220466704-Acetoxy-3,5-dimethoxy-2-nitrobenzoic Acid

Product 1

HCID 22046638Methyl 3,5-dimethoxy-4-hydroxy-2-nitrobenzoateYield 91.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A catalytic amount of DMF (5 drops) was added to a solution of oxalyl chloride (6.3 g, 49.8 mmol) and o-nitrobenzoic acid 83 (12.4 g, 45.2 mmol) in anhydrous THF (100 mL) and the reaction mixture allowed to stir at room temperature for 16 h. The resulting acid chloride was quenched dropwise with anhydrous methanol (100 mL) at 0° C. The reaction mixture was treated with potassium carbonate and allowed to stir at room temperature for 3 h. Excess solvent was removed by rotary evaporation at reduced pressure and the residue dissolved in water. The aqueous solution was acidified to pH 8 and the resulting white precipitate was collected by filtration, washed with water (2×100 mL) and dried to afford the product as an off-white solid (10.6 g, 83%). H1 NMR (270 MHz, CDCl3) δ10.07 (br s, 1H), 7.26 (s, 1H), 3.97 (s, 3H), 3.91 (s, 3H), 3.85 (s, 3H).

Workup

  1. customThe resulting acid chloride was quenched dropwise with anhydrous methanol (100 mL) at 0° C
  2. additionThe reaction mixture was treated with potassium carbonate
  3. stirringto stir at room temperature for 3 h
  4. customExcess solvent was removed by rotary evaporation at reduced pressure
  5. dissolutionthe residue dissolved in water
  6. filtrationthe resulting white precipitate was collected by filtration
  7. washwashed with water (2×100 mL)
  8. customdried

Sources & evidence

ORD record
ord-d9373a0a092d4d74b35e5938dca8c8ba
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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