Ethyl Acetate → HCID 67618572, compound

HRID 1600171Notes

Reaction equation

HRID 1600171 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(OCC)(=O)C>CCOCC>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([NH:21][N:22]=[CH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:19][CH:20]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3310889(4-Nitrophenyl)hydrazineHCID 101977823-(4-Fluorophenyl)propanal

Product 1

HCID 67618572HCID 67618572, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-(4-fluorophenyl)propanal (7.0 g) in ether (50 ml) was addedto a stirred suspension of 4-nitrophenylhydrazine (7.0 g) in ether (1 50 ml), followed by sufficient ethyl acetate to achieve a clear solution. Thesolution was filtered and evaporated and the residue was crystallised from ethyl acetate/hexane to give the title compound (5.48 g), m.p. 125°-127° C. Found: C,62.81; H,4.87; N,14.44. C15 H14FN3O2 requires: C,62.71; H,4.91; N,14.63%.

Workup

  1. filtrationThesolution was filtered
  2. customevaporated
  3. customthe residue was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b36e35623acd4eb1b70a496f4f90260f
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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