Butyl bromide → 6-(4-n-Butoxy-3-methoxyphenyl)-3[2H]pyridazinone

HRID 247389ノート

反応式

HRID 247389 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[O:15][CH3:16].Br[CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[O:15][CH3:16])[CH2:19][CH2:20][CH3:21]

参加物

5

反応物 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 1358334136-(3-Methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)tetrahydropyridazin-3(2H)-one

生成物 1

HCID 201606496-(4-n-Butoxy-3-methoxyphenyl)-3[2H]pyridazinone

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

11.0 g of 6-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-3[2H]pyridazinone are heated under reflux together with 8.2 g of 1-bromobutane and 8.3 g of potassium carbonate in 150 ml of anhydrous acetone for 20 hours. Thereafter, the starting compound can no longer be detected by thin-layer chromatography. The suspension is filtered hot, the filter cake is washed out with hot acetone and the filtrates are combined and evaporated in vacuo. The semi-solid residue [6-(4-n-butoxy-3-methoxyphenyl)4,5-dihydro-3[2H]pyridazinone]is taken up in 50 ml of ethanol, 10.0 g of sodium hydroxide in 200 ml of water and 14.6 g of sodium meta-nitrobenzenesulfonate are added and the mixture is heated under reflux for 2 hours. After cooling, it is acidified to pH 1-2 with concentrated hydrochloric acid, the crystalline solid is filtered off with suction and the solution is extracted several times with chloroform. The residue from the chloroform extract is combined with the crystals and the product is recrystallized from ethanol/ethyl acetate. 8.7 g (63.7% of theory) of the title compound of m.p. 193° are obtained.

後処理

  1. filtrationThe suspension is filtered hot
  2. washthe filter cake is washed out with hot acetone
  3. customevaporated in vacuo
  4. addition10.0 g of sodium hydroxide in 200 ml of water and 14.6 g of sodium meta-nitrobenzenesulfonate are added
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 2 hours
  7. temperatureAfter cooling
  8. filtrationthe crystalline solid is filtered off with suction
  9. extractionthe solution is extracted several times with chloroform
  10. extractionThe residue from the chloroform extract
  11. customthe product is recrystallized from ethanol/ethyl acetate

出典と根拠

ORDレコード
ord-598d2a6548c54131997f71a163e4bc94
出典データセット
uspto-grants-1987_11
特許番号
US04707481

反応ノート

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