Hydrazine hydrate (1:1) → [6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)-pyridazin-3-yl]hydrazine

HRID 429743노트

반응식

HRID 429743 반응식
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1.O.[NH2:16][NH2:17]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:16][NH2:17])=[CH:6][C:7]=1[N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 183533373,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine

생성물 1

HCID 18353340[6-chloro-5-(3,6-dihydro-2H-pyridin-1-yl)-pyridazin-3-yl]hydrazine수율 88%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

A mixture of 3,6-dichloro-4-(3,6-dihydro-2H-pyridin-1-yl)pyridazine (1.7 g, 7.4 mmol) and hydrazine hydrate (2.2 ml) in dioxan was stirred and heated at reflux under nitrogen for 24 hours. Upon cooling the dioxan was removed in vacuo and the residue was partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane (×3). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was triturated with ether/MeOH and dried in vacuo to afford the title pyridazine (1.5 g, 88%). 1H NMR (250 MHz, d6-DMSO) 7.8 (1H, br s), 6.48 (1H, s), 5.76 (2H, m), 4.21 (2H, br s), 3.51 (2H, m), 3.24 (2H, m), 2.16 (2H, m). MS (ES+) 226 [MH]+, 228 [MH]+.

후처리

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 24 hours
  3. customwas removed in vacuo
  4. customthe residue was partitioned between dichloromethane and water
  5. extractionThe aqueous was further extracted with dichloromethane (×3)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was triturated with ether/MeOH
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-6aa1386310a7485b993da535d56de599
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319924B1

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