Hydrochloric Acid → HCID 178510213, compound

HRID 878538Notes

Reaction equation

HRID 878538 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][NH:10]/[CH:11]=[CH:12]/[C:13]([O:15]CC)=O)[CH:4]=1)#[N:2].CC([O-])(C)C.[K+].Cl>CCO>[OH:15][C:13]1[N:9]([C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][N:6]=2)[N:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 86725509ethyl (2E)-3-[2-(4-cyanopyridin-2-yl)hydrazinyl]prop-2-enoate

Product 1

HCID 178510213HCID 178510213, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (2E)-3-[2-(4-cyanopyridin-2-yl)hydrazinyl]prop-2-enoate (2.0 g, 8.62 mmol) in 30 mL EtOH was added t-BuOK (1.93 g, 17.24 mmol) at 0-5° C. The mixture was stirred for 3 days at rt. The mixture was adjusted to pH=6 with 1 N HCl with cooling. The mixture was extracted with EtOAc (3×100 mL). The organic layers were washed with 200 ml brine, dried over Na2SO4, and concentrated to dryness. The resultant residue was stirred with PE/EtOAc (10/10 mL) for 30 min and filtered to give the title compound (500 mg, 31%) as a red solid. 1H NMR (400 MHz, CDCl3): δ 4.63 (1H, s), 7.12 (1H, dd, J=4.8, 1.2 Hz), 7.16 (1H, s), 8.35 (1H, d, J=4.4 Hz), 8.43 (1H, s). [M+H] Calc'd for C9H6N4O, 187; Found, 187.

Workup

  1. temperaturewith cooling
  2. extractionThe mixture was extracted with EtOAc (3×100 mL)
  3. washThe organic layers were washed with 200 ml brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. stirringThe resultant residue was stirred with PE/EtOAc (10/10 mL) for 30 min
  7. filtrationfiltered

Sources & evidence

ORD record
ord-430eca6393fd47d59d65f59db1e66a55
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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