Ethanol → 2-[(Z)-C-(3-bromophenyl)-N-(tert-butylamino)carbonimidoyl]pyridin-3-ol
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]([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]Participants
6
Procedure
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).
Workup
- temperaturewas refluxed for 5 hours
- extractionsubjected to extraction with ethyl acetate
- washThe extract was washed with water
- dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
- customby evaporating the solvent under reduced pressure
- customThe residue was purified by means of a silica gel column (ethyl acetate--hexane)
Sources & evidence
- ORD record
- ord-2a6d8d69912b45f98cfc07f8d08e9f3f
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05891895
Reaction notes
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