Hydrochloric Acid → HCID 58349312, compound

HRID 1908979Notes

Reaction equation

HRID 1908979 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:3]1[CH:8]=[CH:7][N:6]=C(C#N)[CH:4]=1.[OH-:17].[Na+].Cl.[CH2:20]([OH:22])[CH3:21]>CO.C(Cl)Cl>[CH3:1][N:2]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:3]1[CH:8]=[CH:7][N:6]=[C:21]([C:20]([OH:17])=[O:22])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 583492584-(Methyl(pyridin-3-yl)amino)picolinonitrile

Product 1

HCID 58349312HCID 58349312, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Compound 11 (0.473 g, 2.25 mmol, 1.00 eq) was dissolved in ethanol (10 mL) and 1N NaOH (5 mL) was added. The mixture was refluxed for 18 h and after cooling the reaction was neutralized with 1N HCl (5 mL) and the reaction was concentrated in vacuo. The crude reaction was dissolved in 10% MeOH/CH2Cl2 and the undissolved salt was filtered off and the solvents were removed in vacuo to afford 0.461 g (89%) of the title compound as a tan solid: 1H NMR (400 MHz, CDCl3) δ8.65-8.61 (m, 2H), 8.12 (d, J=6.7 Hz, 1H), 7.88 (ddd, J=8.1, 2.5, 1.6 Hz, 1H), 7.60 (dd, J=8.2, 4.8 Hz 1H), 7.4 (d, J=2.9 Hz, 1H), 6.88 (dd, J=6.7, 2.9 Hz, 1H), 3.46 (s, 3H); [M+1]+: 230.2.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. temperatureafter cooling the reaction
  3. concentrationthe reaction was concentrated in vacuo
  4. customThe crude reaction
  5. filtrationthe undissolved salt was filtered off
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-9d789901edb343ad95df26187d45bb09
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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