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

HRID 640798노트

반응식

HRID 640798 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 106584324,6-Dichloro-3-hydroxy-2-nitrobenzoic acid수율 89%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-afecdddde4604f3388d75d34b6338372
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692011B2

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