Hydrochloric Acid → HCID 12913241, compound

HRID 516685Notes

Reaction equation

HRID 516685 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]#[N:11].[CH2:12]([NH2:14])[CH3:13].Cl>CO>[CH2:12]([NH:14][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]#[N:11])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 113896344-CHLORO-6-METHYL-2-OXO-1,2-DIHYDROPYRIDINE-3-CARBONITRILE

Product 1

HCID 12913241HCID 12913241, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 10 ml microwave vial added 4-chloro-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (750 mg, 4.45 mmol) and methanol (1 mL) then added ethylamine (5.56 mL, 11.12 mmol). One drop on conc. HCl was added and the vial was capped and the reaction was microwaved to 120° C. for 1 hr. The reaction was cooled and the solid was filtered and washed with cold MeOH. Gave 4-(ethylamino)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (500 mg, 2.77 mmol, 62.2% yield) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.05 (br. s., 1H) 7.11 (br. s., 1H) 5.78 (br. s., 1H) 3.22-3.32 (m, 2H) 2.11 (s, 3H) 1.10 (t, J=7.07 Hz, 3H) MS(ES) [M+H]+ 177.8.

Workup

  1. customthe vial was capped
  2. customthe reaction was microwaved to 120° C. for 1 hr
  3. temperatureThe reaction was cooled
  4. filtrationthe solid was filtered
  5. washwashed with cold MeOH

Sources & evidence

ORD record
ord-18080b90179944ebac4a2747406dc010
Source dataset
uspto-grants-2015_08
Patent number
US09114141B2

Reaction notes

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