Ethanol → (Z)-2-(3-bromo-alpha-t-butoxyiminobenzyl)-3-hydroxypyridine

HRID 442729노트

반응식

HRID 442729 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]([O:22][NH2:23])([CH3:21])([CH3:20])[CH3:19].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]\[O:22][C:18]([CH3:21])([CH3:20])[CH3:19].[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]/[O:22][C:18]([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 702EthanolHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 110331762-(3-Bromobenzoyl)-3-hydroxypyridine

생성물 2

HCID 135450983(Z)-2-(3-bromo-alpha-t-butoxyiminobenzyl)-3-hydroxypyridineHCID 135490885(E)-2-(3-bromo-alpha-t-butoxyiminobenzyl)-3-hydroxypyridine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-(3-bromobenzoyl)-3-hydroxypyridine (1.78 g), O-t-butylhydroxylamine hydrochloride (1.19 g) and ethanol (50 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-butoxyiminobenzyl)-3-hydroxypyridine (0.83 g) and (Z)-2-(3-bromo-α-t-butoxyiminobenzyl)-3-hydroxypyridine (0.83 g) and (Z)-2-(3-bromo-α-t-butoxyiminobenzyl)-3-hydroxypyridine (1.12 g) (compounds 2 and 1). In substantially the same manner as above, compounds 5, 6, 10, 13, 14, 18 to 24 were produced. Physical properties and spectrum data of these compounds and those produced in the following Examples are shown in Table 7 to Table 11.

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-5ee6b3fe76aa47d1b081a1a0cb37b1b3
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891895

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