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

HRID 442733노트

반응식

HRID 442733 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2a6d8d69912b45f98cfc07f8d08e9f3f
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891895

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