Hydrochloric Acid → 2-Methoxy-4-(methylamino)-5-nitrobenzoic acid

HRID 2293532Notes

Reaction equation

HRID 2293532 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:14][CH3:15])[CH:3]=1.[OH-].[Na+].Cl.CO.[CH3:21][NH2:22]>>[CH3:15][O:14][C:4]1[CH:3]=[C:2]([NH:22][CH3:21])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 128487494-Chloro-2-methoxy-5-nitrobenzoic acidHCID 57454252Monomethylamine methanol

Product 1

HCID 109879372-Methoxy-4-(methylamino)-5-nitrobenzoic acid

Procedure

A 1.00 g portion of 4-chloro-2-methoxy-5-nitrobenzoic acid and 0.52 g of sodium hydroxide were dissolved in 20 ml of 40% methylamine methanol solution, followed by stirring at room temperature for 12 hours. After completion of the reaction, the reaction solution was poured on crushed ice and adjusted to pH 4 with 6N hydrochloric acid aqueous solution. The thus precipitated product of interest was collected by filtration, washed with water and dried under a reduced pressure and then the resulting crude product was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 0.30 g of 2-methoxy-4-methylamino-5-nitrobenzoic acid.

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction solution was poured
  3. customon crushed ice
  4. filtrationThe thus precipitated product of interest was collected by filtration
  5. washwashed with water
  6. customdried under a reduced pressure
  7. customthe resulting crude product was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-c215394ecce14f8f86158ae691998e20
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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