Hydroxyamine hydrochloride → (NZ)-N-[(5-fluoro-2-methoxyphenyl)-[3-fluoro-4-(4-methyl-3-pyridinyl)-2-pyridinyl]methylidene]hydroxylamine

HRID 593754Notes

Reaction equation

HRID 593754 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8]([C:10]2[C:15]([F:16])=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[CH:13]=[CH:12][N:11]=2)=O)[CH:7]=1.Cl.[NH2:27][OH:28]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6](/[C:8](/[C:10]2[C:15]([F:16])=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[CH:13]=[CH:12][N:11]=2)=[N:27]/[OH:28])[CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86730410(5-Fluoro-2-methoxyphenyl)(3'-fluoro-4-methyl-3,4'-bipyridin-2'-yl)methanone

Product 1

HCID 136622532(NZ)-N-[(5-fluoro-2-methoxyphenyl)-[3-fluoro-4-(4-methyl-3-pyridinyl)-2-pyridinyl]methylidene]hydroxylamineYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (5-fluoro-2-methoxyphenyl)(3′-fluoro-4-methyl-3,4′-bipyridin-2′-yl)methanone (0.024 g, 0.071 mmol) and hydroxylamine hydrochloride (0.033 g, 0.480 mmol) in pyridine (Volume: 0.353 ml) was refluxed for 3 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, 0-95% EtOAc in hexanes over 15 min, tr=0.5, 1.5 2.5 min) gave the title compound (22 mg, 0.061 mmol, 87% yield) as a yellow residue. ESI MS (M+H)+=356.1.

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, 0-95% EtOAc in hexanes over 15 min, tr=0.5, 1.5 2.5 min)

Sources & evidence

ORD record
ord-6f7b6cf0de7b4f5aa0b6bd6e8fd7d258
Source dataset
uspto-grants-2016_01
Patent number
US09242967B2

Reaction notes

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