Pyridine → HCID 72465828, compound

HRID 852073Notes

Reaction equation

HRID 852073 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O.Cl.[NH2:20][OH:21].N1C=CC=CC=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[N:20][OH:21]

Participants

4

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 17906364HCID 17906364, compound

Product 1

HCID 72465828HCID 72465828, compoundYield 99%

Conditions

Temperature
100 °C

Procedure

Mix (2,4-difluoro-phenyl)-(4-methoxy-phenyl)-methanone (257 g, 1.04 mol), hydroxylamine hydrochloride (143.9 g, 2.07 mol) and pyridine (1.29 L, 15.89 mol), under a nitrogen atmosphere and heat (100° C.). Cool reaction mixture to room temperature and concentrate to an oily residue. Partition residue between ethyl acetate (2700 mL) and water (1600 mL). Wash organic layer with 1 N HCl solution (2×800 mL), water (2×1 L), saturated sodium chloride (1 L), dry (MgSO4) and concentrate to give the title compound as an oil. (270.84 g, 99% Yield): 1H NMR (CDCl3, 200 MHz) δ 3.8-3.82 (2 s, 3H), 6.8-7.0 (m, 3H), 7.2 (m, 1H), 7.4 (d, 2H), 7.5 (d, 1H), 8.4-8.6 (br s, 1H). Purity by LC/MS (APCl)=100% area, [M+H]+=264 m/e.

Workup

  1. temperatureCool
  2. customreaction mixture to room temperature
  3. concentrationconcentrate to an oily residue
  4. dry with materialWash organic layer with 1 N HCl solution (2×800 mL), water (2×1 L), saturated sodium chloride (1 L), dry (MgSO4)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-98a3536d31ae46d9b61bb2a7462be943
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

Loading…