Pentamethylbenzene → 2-amino-N-(5-chloro-2-pyridinyl)-3-hydroxybenzamide

HRID 219437

反応式

HRID 219437 の反応式
C([O:8][C:9]1[C:10]([N+:25]([O-])=O)=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13])C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1>FC(F)(F)C(O)=O>[NH2:25][C:10]1[C:9]([OH:8])=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13]

参加物

4

反応物 2

HCID 12784PentamethylbenzeneHCID 180011353-benzyloxy-N-(5-chloro-2-pyridyl)-2-nitrobenzamide

生成物 1

HCID 180011272-amino-N-(5-chloro-2-pyridinyl)-3-hydroxybenzamide収率 89.6%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
40 °C

実験手順

To 7.44 g of 3-benzyloxy-N-(5-chloro-2-pyridyl)-2-nitrobenzamide were added 40 ml of trifluoroacetic acid and 3.72 g of pentamethylbenzene and the mixture was stirred at 40° C. for one night. The reaction solution was concentrated in vacuo, a saturated aqueous solution of sodium bicarbonate was added to the resulting residue to such an extent that the residue did not become alkaline and the mixture was extracted with chloroform. The organic layer was extracted with a 1N aqueous solution of sodium hydroxide and the aqueous layer was acidified by adding hydrochloric acid thereto and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and 200 ml of an ethanolic suspension of Raney nickel was added to the resulting residue. The mixture was stirred a hydrogen atmosphere for 6 hours, N,N-dimethylformamide was added and the insoluble matters were filtered off. The solvent was evaporated in vacuo and water was added to the resulting residue. The resulting precipitate was filtered and dried in vacuo to give 4.58 g of 2-amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide.

後処理

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additiona saturated aqueous solution of sodium bicarbonate was added to the resulting residue to such an extent that the residue
  3. extractionthe mixture was extracted with chloroform
  4. extractionThe organic layer was extracted with a 1N aqueous solution of sodium hydroxide
  5. additionby adding hydrochloric acid
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated in vacuo and 200 ml of an ethanolic suspension of Raney nickel
  9. additionwas added to the resulting residue
  10. stirringThe mixture was stirred a hydrogen atmosphere for 6 hours
  11. additionN,N-dimethylformamide was added
  12. filtrationthe insoluble matters were filtered off
  13. customThe solvent was evaporated in vacuo and water
  14. additionwas added to the resulting residue
  15. filtrationThe resulting precipitate was filtered
  16. customdried in vacuo

出典と根拠

ORDレコード
ord-a4c669ec6dca4913ae9eb46a8375d9dc
出典データセット
uspto-grants-2012_06
特許番号
USRE043481E1

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