Ethanol → 2-[(Z)-C-(3-bromophenyl)-N-(tert-butylamino)carbonimidoyl]pyridin-3-ol

HRID 442733ノート

反応式

HRID 442733 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=O.Cl.[C:18]([NH:22][NH2:23])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)/[C:5](/[C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=1)=[N:23]/[NH:22][C:18]([CH3:21])([CH3:20])[CH3:19]

参加物

6

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 110331762-(3-Bromobenzoyl)-3-hydroxypyridine

生成物 1

HCID 1364448522-[(Z)-C-(3-bromophenyl)-N-(tert-butylamino)carbonimidoyl]pyridin-3-ol収率 24.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-(3-bromobenzoyl)-3-hydroxypyridine (0.79 g), t-butylhydrazine hydrochloride (0.53 g), triethylamine (1.2 mL) and ethanol (13 mL) was refluxed for 5 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate), followed by evaporating the solvent under reduced pressure. The residue was purified by means of a silica gel column (ethyl acetate--hexane) to afford (E)-2-(3-bromo-α-t-butylhydrazinobenzyl)-3-hydroxypyridine (0.60 g) and (Z)-2-(3-bromo-α-t-butylhydrazonobenzyl)-3-hydroxypyridine (0.24 g) (compounds 27 and 26).

後処理

  1. temperaturewas refluxed for 5 hours
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. customby evaporating the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column (ethyl acetate--hexane)

出典と根拠

ORDレコード
ord-2a6d8d69912b45f98cfc07f8d08e9f3f
出典データセット
uspto-grants-1999_04
特許番号
US05891895

反応ノート

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