Ethanol → 1-(1-Ethoxyethylidene)-2-(4-nitrophenyl)hydrazine

HRID 2106758Notes

Reaction equation

HRID 2106758 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)C.Cl.[C:16](=N)([O:18][CH2:19][CH3:20])[CH3:17]>O>[CH2:16]([O:18][C:19](=[N:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:20])[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 539405891-(1-Ethoxyethylidene)-2-(4-nitrophenyl)hydrazineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (ice-bath) mixture of 15 parts of 1-(4-nitrophenyl)hydrazine and 160 parts of absolute ethanol were added 13.5 parts of ethyl ethanimidate hydrochloride. After stirring for 3 hours while cooling, the reaction mixture was poured into water. The precipitated product was filtered off, washed with water and dried, yielding 19 parts (85%) of 1-(1-ethoxyethylidene)-2-(4-nitrophenyl)hydrazine; mp. 101.8° C. (int. 18).

Workup

  1. temperaturecooled
  2. stirringAfter stirring for 3 hours
  3. temperaturewhile cooling
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-93c3f25e38054d6ab7bc7d31da175792
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

Loading…