Pentylhydrazine → HCID 76629633, compound

HRID 2077265Notes

Reaction equation

HRID 2077265 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH:5]=O)[CH3:2].[CH2:8]([NH:13][NH2:14])[CH2:9][CH2:10][CH2:11][CH3:12]>C(O)C>[CH2:1]([O:3][C:4](=[O:7])[CH:5]=[N:14][NH:13][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 14247PentylhydrazineHCID 70211Ethyl oxoacetate

Product 1

HCID 76629633HCID 76629633, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a magnetically stirred solution of oxo-acetic acid ethyl ester (35.08 ml, 177 mmol; 50% solution in toluene) in ethanol (450 ml) was added n-pentylhydrazine (21.7 g, 212 mmol) and the resulting solution was heated at 80° C. for 16 hours. The obtained mixture was allowed to attain room temperature and concentrated. The resulting residue was taken up in ethylacetate and water. The organic layer was separated and subsequently dried over MgSO4, filtered and concentrated to give (pentylhydrazono)acetic acid ethyl ester (Intermediate II-1) (32.2 gram, 93% yield) as a purple colored oil. 1H-NMR (400 MHz, CDCl3) δ 0.87-0.94 (m, 3H), 1.25-1.42 (m, 7H), 1.55-1.68 (m, 2H), 3.17-3.23 (m, 1H), 3.35-3.45 (m, 1H), 4.28 (q, J=7, 2H), 6.51 (br s, 1H), 6.72 (s, 1H).

Workup

  1. customto attain room temperature
  2. concentrationconcentrated
  3. customThe organic layer was separated
  4. dry with materialsubsequently dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3902c89133f54e07afd1a99e5611efde
Source dataset
uspto-grants-2011_04
Patent number
US07928134B2

Reaction notes

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