Water → N-(2-propynyl)-3-chloro-6-nitroindazole

HRID 1075973

反応式

HRID 1075973 の反応式
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:20](Br)#[C:21][CH3:22].O>CC(C)=O>[CH2:22]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:2]([Cl:1])=[N:3]1)[C:21]#[CH:20]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1372791-Propyne, 1-bromo-HCID 178526457HCID 178526457、化合物

生成物 1

HCID 21439192N-(2-propynyl)-3-chloro-6-nitroindazole

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Compounds III-A, III-B and III-D were prepared by a modification of the procedure of Zaugg, Swett and Stone (5). In a stirred solution of sodium ethylate prepared from 0.23 g (0.01 mol) of sodium metal and 50 ml of absolute ethanol was dissolved 0.01 mole of the appropriate nitro- or chloroindazole. To such solution was added 2.38 g (0.02 mol) of propynyl bromide, and the reaction mixture was stirred for twenty-four hours at room temperature during which time sodium bromide precipitated. The reaction mixture was poured into 100 ml of water and the oily layer was extracted with ether. The ether layer was separated, washed with water, 10% potassium hydroxide solution, saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. The residue was recrystallized from 95% ethanol to give the desired N-(2-propynyl) indazoles. To prepare compound III-C, a mixture of 10 g (0.043 mol) of 3-chloro-6-nitroindazole, 6.9 g (0.043 mol) of anhydrous potassium carbonate and 0.10 g (0.086 mol) of propynyl bromide was placed in 100 ml of acetone. The reaction mixture was refluxed for twenty-four hours, and then poured into 100 ml of water. The oily layer was extracted with ether, and the ether layer was separated, washed with water, 10% sodium hydroxide solution, saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. The residue was recrystallized from 95% ethanol to give N-(2-propynyl)-3-chloro-6-nitroindazole.

後処理

  1. customTo prepare compound III-C
  2. temperatureThe reaction mixture was refluxed for twenty-four hours
  3. extractionThe oily layer was extracted with ether
  4. customthe ether layer was separated
  5. washwashed with water, 10% sodium hydroxide solution, saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from 95% ethanol

出典と根拠

ORDレコード
ord-0e68fc6b61764fcc93c677e9c6dc3e88
出典データセット
uspto-grants-1976_05
特許番号
US03954793

関連ノート

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