Phosphorus oxychloride → ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate

HRID 439724

反応式

HRID 439724 の反応式
[C:1]([C:3]1(O[Si](C)(C)C)[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][C:8]2[N:7]([CH3:17])[N:6]=[C:5]([CH3:18])[C:4]1=2)#[N:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([C:3]1[C:4]2[C:5]([CH3:18])=[N:6][N:7]([CH3:17])[C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:2]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 22402969ethyl 4-cyano-4,5,6,7-tetrahydro-1,3-dimethyl-4-(trimethylsilyloxy)-1H-indazole-5-carboxylate

生成物 1

HCID 22402928ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate収率 53.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of ethyl 4-cyano-4,5,6,7-tetrahydro-1,3-dimethyl-4-(trimethylsilyloxy)-1H-indazole-5-carboxylate (28.1 g, 0.119 mol) in pyridine is mixed with phosphorus oxychloride (43.0 mL, 0.461 mol), stirred for 5 hours at reflux temperature and concentrated in vacuo. The resultant black residue is diluted with ethyl acetate and water and treated with sodium bicarbonate to pH 6. The phases are separated, the organic phase is set aside, and the aqueous phase is extracted with ethyl acetate. The organic phases are combined, washed with aqueous sodium bicarbonate and water, dried (MgSO4) and concentrated in vacuo to give a black residue. The residue is triturated under ethyl acetate to give the title product as a tan solid (15.5 g, 52.9%), identified by 1HNMR and IR spectroscopy.

後処理

  1. temperatureat reflux temperature
  2. concentrationconcentrated in vacuo
  3. additionThe resultant black residue is diluted with ethyl acetate and water
  4. additiontreated with sodium bicarbonate to pH 6
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. washwashed with aqueous sodium bicarbonate and water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give a black residue
  11. customThe residue is triturated under ethyl acetate

出典と根拠

ORDレコード
ord-25104ed23134410ebadbd8b76540278c
出典データセット
uspto-grants-1996_05
特許番号
US05516751

関連ノート

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