Ammonium Chloride → HCID 58153490, compound

HRID 508481Notes

Reaction equation

HRID 508481 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Cl:11])=[C:4]([O:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[N:3]=1.[Cu][C:20]#[N:21].[Cl-].[NH4+]>C(#N)C>[Cl:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:20]#[N:21])=[N:3][C:4]=1[O:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58153355HCID 58153355, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 58153490HCID 58153490, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 10 ml single-necked round-bottomed flask equipped with an efficient condensor, 2-bromo-5-chloro-6-(4-methyl-pentyloxy)-3-nitro-pyridine (200 mg) is dissolved in dry acetonitrile (3.00 ml). To the reulting yellow solution, copper(I) cyanide (109 mg) is added. The resulting suspension is stirred under heating to reflux for 6 hours whereupon a brown solution is obtained. The progress of the transformation is followed by GC-MS. The mixture is allowed to reaxch ambient temperature. Saturated ammonium chloride solution (20 ml) along with some ice is then added and the mixture extracted with ether (2×20 ml). The combined organic phases are then dried over sodium sulfate, filtered and the solvent is removed in vacuo to give 150 mg of the title compound in the form of a yellow oil (89%).

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 6 hours whereupon a brown solution
  3. customis obtained
  4. customto reaxch ambient temperature
  5. extractionthe mixture extracted with ether (2×20 ml)
  6. dry with materialThe combined organic phases are then dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0d7aad0ce8f6479cb4995103c5923a39
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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