Hydrochloric Acid → 2-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-one

HRID 2239329노트

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HRID 2239329 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](O)=[O:14])=[C:10]([CH:16]=O)[CH:9]=2)=[CH:4][CH:3]=1.O.[NH2:19][NH2:20].Cl.C([O-])(O)=O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:14])[NH:19][N:20]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 593044065-(4-Chlorophenyl)-3-formylthiophene-2-carboxylic acid

생성물 1

HCID 115798042-(4-Chlorophenyl)thieno[2,3-d]pyridazin-7(6H)-one수율 72.7%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
82 °C

실험 절차

To a stirred solution of 5-(4-chlorophenyl)-3-formylthiophene-2-carboxylic acid (3 g, 0.011 mol) in ethanol (30 ml) was added hydrazine hydrate (0.65 ml, 0.013 mol) in small drops. To this was added conc. HCl (1.8 ml, 0.058 mol) in a dropwise manner and heated to 82° C. for 2 days. The reaction mixture was allowed to cool down and 10% NaHCO3 (5 ml) was added slowly until pH=8. The solid was filtered, washed with water (200 ml) and dried to afford 2.1 g (71%) of the title compound. Rf=0.5 (CHCl3:MeOH, 8:2). 1H NMR (400 MHz, DMSO-d6) δ 12.98 (bs, 1H), 8.39 (s, 1H), 7.98 (s, 1H), 7.88 (d, 2H, J=8.6 Hz), 7.59 (d, 2H, J=8.6 Hz).

후처리

  1. temperatureto cool down
  2. filtrationThe solid was filtered
  3. washwashed with water (200 ml)
  4. customdried

출처 및 근거

ORD 기록
ord-54844651b2ae45009d9a509b1740fa2e
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723331B2

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