Triethylamine → HCID 68840644, compound

HRID 2099506Notes

Reaction equation

HRID 2099506 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].C(N(CC)CC)C.[CH2:16]([O:18]/[CH:19]=[CH:20]/[C:21](Cl)=[O:22])[CH3:17]>C1COCC1>[CH2:16]([O:18]/[CH:19]=[CH:20]/[C:21]([NH:2][NH:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:22])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 786452-HydrazinopyridineHCID 53255003-Ethoxyacryloyl chloride

Product 1

HCID 68840644HCID 68840644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 2-hydrazinopyridine (10.74 g, 98.4 mmol) and triethylamine (9.94 g, 98.4 mmol) in THF (100 mL) was added crude (2E)-3-ethoxyprop-2-enoyl chloride (based on 100% yield of previous step) dropwise. The resulting reaction mixture was allowed to warm to ambient temperature over 2 h and then heated at reflux for a further 5 h. The reaction mixture was quenched with water (50 mL), extracted with EtOAc (3×50 mL) and washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo, purified using liquid chromatography on silica gel eluting with EtOAc to afford (2E)-3-ethoxy-N′-pyridin-2-ylprop-2-enohydrazide as a brown oil. 1H NMR (CD3Cl, 300 MHz) δ 9.19 (br, 1H), 8.08 (d, 1H), 7.59˜7.44 (m, 3H), 6.75˜6.69 (m, 2H), 5.34 (d, 1H), 3.81 (q, 2H), 1.27 (t, 3H). MS (ESI) 208 (M++H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureat reflux for a further 5 h
  4. customThe reaction mixture was quenched with water (50 mL)
  5. extractionextracted with EtOAc (3×50 mL)
  6. washwashed with brine
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified

Sources & evidence

ORD record
ord-b5d1027f0933432a8b9d448fbb641440
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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