Ammonium Chloride → HCID 58336735, compound

HRID 2358977Notes

Reaction equation

HRID 2358977 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1.C[O-].[Na+].[Cl-].[NH4+:24]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([C:18]([NH2:24])=[NH:19])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 51050006HCID 51050006, compound

Product 1

HCID 58336735HCID 58336735, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

With heating, 0.7 g (2.8 mmol) of 6-(1-pyridin-3-yl-1H-pyrazol-4-yl)pyridine-2-carbonitril was dissolved in 150 ml of abs. methanol, and 1 ml of a solution of sodium methoxide in methanol (30%, corresponds to 5.4 mmol) was added. The mixture was stirred at 65° C. until the thin-layer chromatogram (TLC) showed complete conversion, 1.5 g of ammonium chloride was added and the mixture was concentrated. The residue was boiled twice with in each case 30 ml of ethanol, the hot mixture was filtered and the combined filtrates were concentrated slightly. The mixture was allowed to stand at RT for 20 min, and the precipitate formed was filtered off with suction, washed with MTBE and dried on a rotary evaporator.

Workup

  1. temperatureWith heating
  2. additionwas added
  3. concentrationthe mixture was concentrated
  4. filtrationthe hot mixture was filtered
  5. concentrationthe combined filtrates were concentrated slightly
  6. customthe precipitate formed
  7. filtrationwas filtered off with suction
  8. washwashed with MTBE
  9. customdried on a rotary evaporator

Sources & evidence

ORD record
ord-8b074dfb503f418689beb885c9f935e3
Source dataset
uspto-grants-2014_04
Patent number
US08685964B2

Reaction notes

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