2-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone → HCID 72819808, compound

HRID 2117733Notes

Reaction equation

HRID 2117733 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[N:17]([O-])=[O:18].[Na+]>C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:17][OH:18])[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanoneHCID 23668193Sodium Nitrite

Product 1

HCID 72819808HCID 72819808, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

2-(4-Fluorophenyl)-1-pyridin-4-ylethanone (0.04 mol/8.6 g) (prepared as described in example 20, steps (a) and (b)) was dissolved in 80 ml of glacial acetic acid. NaNO2 (0.04 mol/2.76 g), dissolved in the smallest amount of H2O possible, was then added dropwise with ice-cooling and stirring. The mixture was then stirred at 0° C. for another 2 h. 500 ml of H2O were then added, and the mixture was stirred at room temperature for another 1 h. The title compound precipitated as a white powder. The precipitate was filtered off, washed with H2O and dried over P2O5 under reduced pressure. Yield: 5.9 g (60%)

Workup

  1. additionwas then added dropwise with ice-
  2. temperaturecooling
  3. stirringThe mixture was then stirred at 0° C. for another 2 h
  4. stirringthe mixture was stirred at room temperature for another 1 h
  5. customThe title compound precipitated as a white powder
  6. filtrationThe precipitate was filtered off
  7. washwashed with H2O
  8. dry with materialdried over P2O5 under reduced pressure

Sources & evidence

ORD record
ord-22e558d89b33445bb559b41428ac3a28
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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