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Hydrochloric Acid → 5-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxybenzoic Acid

HRID 17513
ノート
印刷プレビュー

反応式

HRID 17513 の反応式
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21].Cl>C1C=CC=CC=1.C(OCC)(=O)C>[Br:12][C:8]1[CH:9]=[C:10]([OH:11])[C:2]([NH:1][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 217551432-Amino-5-bromo-3-hydroxybenzoic Acid

生成物 1

HCID 685848145-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxybenzoic Acid収率 98.4%

試薬・触媒・溶媒 2

HCID 241Benzene
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

2-Amino-5-bromo-3-hydroxybenzoic acid (I-219) (11.92 g, 51.37 mmol) was dissolved in benzene (360 ml), and pyridine (12.5 m, 154.12 mmol) and pivaloyl chloride (19.0 ml, 154.12 mmol) were added at room temperature. After stirred at 85° C. under nitrogen atmosphere for 3.5 hours, this was cooled to room temperature. The solution was fractionated with ethyl acetate and aqueous 1 M hydrochloric acid solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was subjected to column chromatography with silica gel, and the fraction with hexane:ethyl acetate=95:5 gave the entitled compound (15.98 g, 98.4%) as a brown solid.

後処理

  1. temperaturethis was cooled to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away under reduced pressure

出典と根拠

ORDレコード
ord-cc29d5cd193d4f24af7263ab2dc7c705
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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