Ammonia → HCID 86673451, compound

HRID 2362431Notes

Reaction equation

HRID 2362431 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+:12].[NH3:13].[C-:14]#N.[Na+]>O.C(O)C>[NH2:12][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)([CH3:9])[C:14]#[N:13]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 86673451HCID 86673451, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 250 mL round-bottomed flask equipped with a magnetic stirring bar was charged with 1-(6-bromopyridin-2-yl)ethanone (5.00 g, 25.00 mmol), ammonium chloride (1.538 g, 28.7 mmol), ammonia (3.3 mL, 25.00 mmol), ethanol (7.5 mL), and water (6.3 mL). The resulting suspension was treated with sodium cyanide (1.409 g, 28.7 mmol), and the flask was quickly sealed with a rubber stopper. The mixture was stirred overnight. The reaction was extracted with dichloromethane (3×), the combined organic layer was washed with water to remove the remaining sodium cyanide, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to afford title compound (quant.) as yellowish sticky oil residue which was used without purification. Mass spec.: 225.9 (MH)+.

Workup

  1. customA 250 mL round-bottomed flask equipped with a magnetic stirring bar
  2. customthe flask was quickly sealed with a rubber stopper
  3. extractionThe reaction was extracted with dichloromethane (3×)
  4. washthe combined organic layer was washed with water
  5. customto remove the remaining sodium cyanide
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06b930f8c5f44badb91007545bc93b44
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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