(Phenylmethyl)hydrazine → 3,4-Dichloro-6-phenylpyridazine

HRID 227821

反応式

HRID 227821 の反応式
[O:1]=[C:2](CCC1C=CC=CC=1)C(O)=O.C1(CNN)C=CC=CC=1.[Cl:23][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[Cl:30].[CH3:37][O-:38].[Na+]>CO>[Cl:23][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[Cl:30].[CH3:2][O:1][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[O:38][CH3:37].[CH3:2][O:1][C:24]1[N:25]=[N:26][C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][C:29]=1[Cl:30]

参加物

8

反応物 4

HCID 11157(Phenylmethyl)hydrazineHCID 697322-Oxo-4-phenylbutyric acidHCID 10942334Sodium MethoxideHCID 131632313,4-Dichloro-6-phenylpyridazine

生成物 3

HCID 131632313,4-Dichloro-6-phenylpyridazineHCID 13342056HCID 13342056、化合物HCID 667319983-Methoxy-4-chloro-6-phenylpyridazine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
65 °C

実験手順

3,4-Dichloro-6-phenylpyridazine was synthesized from □-oxobenzenebutanoic acid and 1-(phenylmethyl)hydrazine in 2 steps according to a procedure by Sircar (Sircar, I. J Het. Chem. 1983, 20,1473-1476.) 3,4-Dichloro-6-phenylpyridazine (100 mg, 0.44 mmol) was combined with sodium methoxide (1.1 mL of a 0.50M solution in methanol, 0.55 mmol, 1.25 equiv.) and methanol (296 μl, 1.5M) in a resealable tube and heated to 65° C. for 1 hour. The methanol was evaporated in vacuo, and water was added to the residue. The mixture was extracted with DCM, dried over K2CO3, filtered and concentrated in vacuo, to afford 3,4-dimethoxy-6-phenylpyridazine and 3-methoxy-4-chloro-6-phenylpyridazine, the title compound, as a solid.

後処理

  1. customThe methanol was evaporated in vacuo, and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with DCM
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-667bead50e7a433e8d7e7c138df62023
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

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