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

HRID 442729Notes

Reaction equation

HRID 442729 reaction equation
[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]

Participants

6

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5ee6b3fe76aa47d1b081a1a0cb37b1b3
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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