Hydrochloric Acid → 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid

HRID 640798Notes

Reaction equation

HRID 640798 reaction equation
C(N[C:5]1[C:6]([N+:16]([O-:18])=[O:17])=[C:7]([C:11]([Cl:15])=[CH:12][C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])(=O)C.[OH-:19].[K+].Cl>O.C(OCC)(=O)C>[Cl:14][C:13]1[CH:12]=[C:11]([Cl:15])[C:7]([C:8]([OH:10])=[O:9])=[C:6]([N+:16]([O-:18])=[O:17])[C:5]=1[OH:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10379608HCID 10379608, compound

Product 1

HCID 106584324,6-dichloro-3-hydroxy-2-nitrobenzoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-Acetamido-4,6-dichloro-2-nitrobenzoic acid (9.7 g, 0.033 mol) was added to a solution of KOH (18.7 g, 0.034 mol) in H2O (85 mL). The solution was heated under reflux for 18 h and cool to room temperature. Conc HCl was added to adjust the pH to 0. The mixture was diluted with ethyl acetate and H2O and left to stir at room temperature for 30 min. The layers were separated; the aqueous layer was extracted with ethyl acetate (3×), the extracts combined with the original organic layer, washed with brine, dried and concentrated to yield 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid as a dark red solid (7.4 g, 89%); m.p. 188-189° C. (lit. m.p. (Linderberg, M., Hellberg, S., Bjork, S. et al, Eur. J. Med. Chem., 1999, 34, 729-744): 186° C. (dec)).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 18 h
  3. waitleft
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-afecdddde4604f3388d75d34b6338372
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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