Potassium Hydroxide → 1-Amino-3-benzoylpyrrole

HRID 327844

反応式

HRID 327844 の反応式
[C:1]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[NH2:16]OS(O)(=O)=O>CN(C)C=O.O>[NH2:16][N:11]1[CH:12]=[CH:13][C:9]([C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:8])=[CH:10]1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 27732343-Benzoylpyrrole

生成物 1

HCID 199731561-Amino-3-benzoylpyrrole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-benzoylpyrrole (4.92 g) in 50 ml of dry dimethylformamide was added milled potassium hydroxide (8.06 g). Hydroxylamine-O-sulfonic acid (4.23 g) was added to the suspension in 4 portions over a period of 1 hour with stirring at room temperature. After the addition was completed the reaction mixture was stirred for 30 minutes at room temperature, and subsequently diluted with 50 ml of water and extracted with DCM. The combined organic layers were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1), affording starting material (1.44 g) and the desired product as the second fraction. Recrystallization from ethyl ether/hexane gave the product as crystals (1.80 g), which was combined with material obtained from a 36.9 mmol scale reaction and recrystallized from DCM/hexane affording 3.20 g of crystals, m.p. 82°-83° C.

後処理

  1. additionAfter the addition
  2. stirringwas stirred for 30 minutes at room temperature
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1)
  8. customaffording

出典と根拠

ORDレコード
ord-a1adcbf8f2d04b5dad417556397112ed
出典データセット
uspto-grants-1993_12
特許番号
US05274116

関連ノート

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