Ethylenediamine → 2-Cyano-5-(diphenylmethyl)-pyridine

HRID 1390326ノート

反応式

HRID 1390326 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1.C(N)[CH2:22][NH2:23]>CN(C)P(N(C)C)(N(C)C)=O>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1)#[N:23]

参加物

4

反応物 2

HCID 3301EthylenediamineHCID 227487852-Chloro-5-(diphenylmethyl)-pyridine

生成物 1

HCID 227487762-Cyano-5-(diphenylmethyl)-pyridine

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

実験手順

Heat a mixture of 16.5 g. (0.059 mole) of 2-chloro-5-(diphenylmethyl)-pyridine and 10.6 g. (0.059 mole) of cuprous cyanide in 120 ml. of hexamethylphosphoramide with stirring at 210°-220° C. for 7 hours. Pour the cooled reaction mixture into a solution of 200 ml. of ethylenediamine in 500 ml. of water, and extract with benzene. Wash the benzene extracts with 10% aqueous sodium cyanide, then with water, dry, treat with activated charcoal, filter, and concentrate to obtain 2-cyano-5-(diphenylmethyl)-pyridine. This compound is converted directly to the title compound by heating at reflux with 13 g. of potassium hydroxide pellets in 100 ml. water and 200 ml. ethylene glycol for 15 hours. Remove the ethylene glycol and water under reduced pressure, dissolve the residue in water, acidify with concentrated hydrochloric acid, and extract with chloroform. Dry the chloroform extracts. Concentrate the dried extracts to a residue and triturate the residue with isopropyl ether. Filter the solids, dry and recrystallize from ethanol to obtain 5-(diphenylmethyl)picolinic acid, m.p. 189°-191° C.

後処理

  1. temperatureHeat
  2. additiona mixture of 16.5 g
  3. additionPour
  4. customthe cooled reaction mixture into a solution of 200 ml
  5. extractionof water, and extract with benzene
  6. washWash the benzene
  7. dry with materialwith water, dry
  8. additiontreat with activated charcoal
  9. filtrationfilter
  10. concentrationconcentrate

出典と根拠

ORDレコード
ord-3fd9735455b840f69d8ff7d6102c4f33
出典データセット
uspto-grants-1979_02
特許番号
US04138488

反応ノート

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