(3-(Benzyloxy)phenyl)hydrazine hydrochloride → HCID 118497040, compound

HRID 522153Notes

Reaction equation

HRID 522153 reaction equation
[C:1](/[CH:3]=[C:4](\[O-])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:2].[K+].Cl.[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([NH:27][NH2:28])[CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[NH2:2][C:1]1[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:22]=2)[N:28]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=1

Participants

4

Reactant 2

HCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochlorideHCID 20619185HCID 20619185, compound

Product 1

HCID 118497040HCID 118497040, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of potassium (Z)-1-cyano-3-ethoxy-3-oxoprop-1-en-2-olate (3.73 g, 20.82 mmol) in ethanol (100 mL) was added (3-(benzyloxy)phenyl)hydrazine hydrochloride (Preparation 61, 5.22 g, 20.82 mmol) and the reaction was heated at reflux for 24 hours. The reaction was cooled to room temperature, the solid was filtered and the filtrate was concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 20-40% EtOAc in heptanes to afford the title compound (4.76 g, 68%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 hours
  3. filtrationthe solid was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 20-40% EtOAc in heptanes

Sources & evidence

ORD record
ord-323b9740eee740beb221ff9e552b5e5d
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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