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

HRID 2239329ノート

反応式

HRID 2239329 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
82 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-54844651b2ae45009d9a509b1740fa2e
出典データセット
uspto-grants-2010_05
特許番号
US07723331B2

反応ノート

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