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Triethylamine → HCID 178449878, compound

HRID 442734
Notes
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Reaction equation

HRID 442734 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:14])=O.Cl.[C:19]([NH:23][NH2:24])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)/[C:5](=[N:24]\[NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])/[C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:14].[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)/[C:5](/[C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:14])=[N:24]/[NH:23][C:19]([CH3:22])([CH3:21])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 54490127HCID 54490127, compound

Product 2

HCID 178449878HCID 178449878, compoundHCID 178449879HCID 178449879, compound

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A mixture of 2-(3-bromobenzoyl)-3-hydroxypyridine 1-oxide (2.13 g), t-butylhydrazine hydrochloride (3.03 g), triethylamine (3.5 mL) and ethanol (50 mL) was refluxed for 2 hours. The reaction mixture was then poured into a saturated aqueous saline solution, and subjected to extraction with ethyl acetate. The extract was washed with a saturated aqueous saline solution, 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-t-butylhydrazonobenzyl)-3-hydroxypyridine 1-oxide (0.68 g) and (Z)-2-(3-bromo-α-t-butylhydrazonobenzyl)-3-hydroxypyridine 1-oxide (0.79 g) (compounds 29 and 28).

Workup

  1. temperaturewas refluxed for 2 hours
  2. additionThe reaction mixture was then poured into a saturated aqueous saline solution
  3. extractionsubjected to extraction with ethyl acetate
  4. washThe extract was washed with a saturated aqueous saline solution
  5. dry with materialdried (sodium sulfate)
  6. customby evaporating the solvent under reduced pressure
  7. customThe residue was purified by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-6772afe0daa7403abc75ab2e401c2617
Source dataset
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05891895

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes