Hydroxyamine hydrochloride → (NZ)-N-[[3-fluoro-4-(4-methyl-3-pyridinyl)-2-pyridinyl]-(4-fluorophenyl)methylidene]hydroxylamine

HRID 593748Notes

Reaction equation

HRID 593748 reaction equation
[F:1][C:2]1[C:3]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[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.[NH2:25][OH:26]>N1C=CC=CC=1>[F:1][C:2]1[C:3](/[C:15](/[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:25]\[OH:26])=[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

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86730403(3'-Fluoro-4-methyl-3,4'-bipyridin-2'-yl)(4-fluorophenyl)methanone

Product 1

HCID 136622535(NZ)-N-[[3-fluoro-4-(4-methyl-3-pyridinyl)-2-pyridinyl]-(4-fluorophenyl)methylidene]hydroxylamineYield 73.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3′-fluoro-4-methyl-3,4′-bipyridin-2′-yl)(4-fluorophenyl)methanone (0.029 g, 0.093 mmol) and hydroxylamine hydrochloride (0.044 g, 0.636 mmol) in pyridine (Volume: 0.467 ml) was refluxed for 1.5 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 12 min, tr=2 5 min) gave the title compound (22 mg, 0.068 mmol, 72.4% yield) as a yellow solid. ESI MS (M+H)+=326.2.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude material was dissolved in a minimal amount of CH2Cl2
  3. customto be chromatographed (required a few drops of MeOH)
  4. customPurification of the crude material by silica gel chromatography
  5. customan ISCO machine (4 g column, 18 mL/min, 80-100% EtOAc in hexanes over 12 min, tr=2 5 min)

Sources & evidence

ORD record
ord-867fb23782e44652abd9a502916896ed
Source dataset
uspto-grants-2016_01
Patent number
US09242967B2

Reaction notes

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