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

HRID 640798ノート

反応式

HRID 640798 の反応式
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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10379608HCID 10379608、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-afecdddde4604f3388d75d34b6338372
出典データセット
uspto-grants-2010_04
特許番号
US07692011B2

反応ノート

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