Hydroxyamine hydrochloride → (NZ)-N-[[3-fluoro-4-(4-methyl-3-pyridinyl)-2-pyridinyl]-phenylmethylidene]hydroxylamine
Reaction equation
[F:1][C:2]1[C:3]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[CH3:14].Cl.[NH2:24][OH:25]>N1C=CC=CC=1>[F:1][C:2]1[C:3](/[C:15](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:24]\[OH:25])=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[CH3:14]Participants
4
Procedure
A solution of (3′-fluoro-4-methyl-3,4′-bipyridin-2′-yl)(phenyl)methanone (0.025 g, 0.086 mmol) and hydroxylamine hydrochloride (0.040 g, 0.582 mmol) in pyridine (Volume: 0.428 ml) was refluxed for 2.5 hr, allowed to cool to room temperature, and then concentrated in vacuo. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed (required a few drops of MeOH). Purification of the crude material by silica gel chromatography using an ISCO machine (4 g column, 18 mL/min, 80-100% EtOAc in hexanes over 10 min, tr=0.3, 1.5, 2 min) gave the title compound (23.7 mg, 0.076 mmol, 89% yield) as a yellow residue. ESI MS (M+H)+=308.2.
Workup
- concentrationconcentrated in vacuo
- dissolutionThe crude material was dissolved in a minimal amount of CH2Cl2
- customto be chromatographed (required a few drops of MeOH)
- customPurification of the crude material by silica gel chromatography
- customan ISCO machine (4 g column, 18 mL/min, 80-100% EtOAc in hexanes over 10 min, tr=0.3, 1.5, 2 min)
Sources & evidence
- ORD record
- ord-d75e7923e11242c6bca65cc3bb12275b
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242967B2
Reaction notes
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