Acetic Acid → HCID 86725503, compound

HRID 514368Notes

Reaction equation

HRID 514368 reaction equation
C[N:2](C)/[C:3](/[CH3:14])=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=O.[NH:16]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][N:25]=1)[C:21]#[N:22])N.CC(O)=O>CCO>[CH3:14][C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[N:16]([C:18]2[CH:19]=[C:20]([C:21]#[N:22])[CH:23]=[CH:24][N:25]=2)[N:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13812977HCID 13812977, compoundHCID 201187142-Hydrazinylpyridine-4-carbonitrile

Product 1

HCID 86725503HCID 86725503, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2E)-3-(dimethylamino)-1-(4-methylphenyl)but-2-en-1-one (227 mg,1.1 mmol) and 2-hydrazinylisonicotinonitrile (150 mg, 1.1 mmol, PREPARATION 2) in 10 mL EtOH was added 2 mL AcOH. The reaction mixture was heated under reflux conditions overnight before being cooled and concentrated to dryness. The residue was adjusted to pH >8 with saturated aq. K2CO3 and then extracted with EtOAc (3×10 mL). The combined organic layers were washed with 20 mL brine, dried, and concentrated to dryness to give the title compound (170 mg, 55.6%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.38 (6H, s), 6.30 (1H, s), 7.15 (4H, s), 7.33 (1H, d, J=4.0 Hz), 7.78 (1H, s), 8.44 (1H, d, J=4.8 Hz). [M+H] Calc'd for C17H14N4, 275. Found, 275.

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions overnight
  2. temperaturebefore being cooled
  3. concentrationconcentrated to dryness
  4. extractionextracted with EtOAc (3×10 mL)
  5. washThe combined organic layers were washed with 20 mL brine
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6f700d4dd1bd467bac982b2f5ace7b6a
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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