Bromine → 6-(4-pyridinyl)-3(2H)-pyridazinone hydrate

HRID 1659535ノート

反応式

HRID 1659535 の反応式
N1C=CC(C2C=CC(=[O:13])NN=2)=CC=1.[N:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:21][CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:16][CH:15]=1.BrBr>C(O)(=O)C>[OH2:13].[N:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 24408BromineHCID 27276126-(Pyridin-4-yl)pyridazin-3(2H)-oneHCID 127640636-(Pyridin-4-yl)-4,5-dihydropyridazin-3(2H)-one

生成物 1

HCID 127902456-(4-pyridinyl)-3(2H)-pyridazinone hydrate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

B-11. 6-(4-Pyridinyl)-3(2H)-pyridazinone--A 2 liter 3-necked round bottom flask was equipped with a mechanical stirrer, a reflux condenser and a dropping funnel. Into the flask was placed 750 ml. of acetic acid and 16.3 g. of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinone. The mixture was heated on a steam bath for about 20 minutes and then a solution containing 50 ml. of bromine and 150 ml. of acetic acid was initially added dropwise. The first 50 ml. of solution was added over a period of about 20 minutes whereupon solid began precipitating. The rest of the bromine solution was then added all at once followed by the addition of 60 ml. more of bromine. Most of the solid redissolved and the resulting mixture was heated with stirring on a steam bath for 6 hours and then allowed to stand at room temperature over the weekend (about 65 hours). A small amount of crystalline solid was filtered off and the filtrate was heated in vacuo to remove the solvent. The remaining residue was treated with 500 ml. of boiling water whereupon most of the residue dissolved. Sodium bisulfite was added to the hot mixture until bubbling of sulphur dioxide ceased. The mixture was made weakly basic to litmus paper by adding sodium bicarbonate. The solid that separated was collected, recrystallized from isopropyl alcohol and dried in a vacuum oven over P2O5 at 45° C. for seventeen hours to produce 6.0 g of 6-(4-pyridinyl)-3(2H)-pyridazinone hydrate (6:1), m.p. 222°-224° C.

後処理

  1. temperatureThe mixture was heated on a steam bath for about 20 minutes
  2. additiona solution containing 50 ml
  3. additionof solution was added over a period of about 20 minutes whereupon solid
  4. custombegan precipitating
  5. additionThe rest of the bromine solution was then added
  6. additionall at once followed by the addition of 60 ml
  7. dissolutionMost of the solid redissolved
  8. temperaturethe resulting mixture was heated
  9. customto stand at room temperature over the weekend (about 65 hours)
  10. filtrationA small amount of crystalline solid was filtered off
  11. temperaturethe filtrate was heated in vacuo
  12. customto remove the solvent
  13. additionThe remaining residue was treated with 500 ml
  14. dissolutionof boiling water whereupon most of the residue dissolved
  15. additionSodium bisulfite was added to the hot mixture
  16. customuntil bubbling of sulphur dioxide
  17. additionby adding sodium bicarbonate
  18. customThe solid that separated
  19. customwas collected
  20. customrecrystallized from isopropyl alcohol
  21. dry with materialdried in a vacuum oven over P2O5 at 45° C. for seventeen hours

出典と根拠

ORDレコード
ord-a44c610f0c0f4a839ad2a8458da185d6
出典データセット
uspto-grants-1981_12
特許番号
US04304777

反応ノート

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