Nitromethane → HCID 54047927, compound

HRID 358547Notes

Reaction equation

HRID 358547 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[C:11]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:10]=[CH:9][C:6]=1[CH:7]=O)(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+].[N+:23]([CH3:26])([O-:25])=[O:24]>>[CH2:14]([N:13]([C:11]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:26][N+:23]([O-:25])=[O:24])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:12]=1)[CH2:16][CH3:17])[CH3:15]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 14794623HCID 14794623, compound

Product 1

HCID 54047927HCID 54047927, compoundYield 36%

Conditions

Temperature
100 °C

Procedure

A solution was prepared by dissolving 23.5 grams (0.10 mol) of 2-acetyloxy-4-(N,N-diethylamino)benzaldehyde in 100 ml of nitromethane, and added with 3 grams of ammonium acetate. The mixture was heated at 100° C. for 5 hours under agitation. The reaction solution was then cooled on a dry ice-acetone bath until crystallization had been completed. The separated solid (crystal) was filtered off and dried in vacuum. The obtained product was recrystallized from acetonitrile for two times. An amount of 10 grams of red crystals was obtained. The yield was 36%.

Workup

  1. customA solution was prepared
  2. temperatureThe reaction solution was then cooled on a dry ice-acetone bath until crystallization
  3. filtrationThe separated solid (crystal) was filtered off
  4. customdried in vacuum
  5. customThe obtained product was recrystallized from acetonitrile for two times

Sources & evidence

ORD record
ord-044d5e6c806a4096998d0ec6e5832f7b
Source dataset
uspto-grants-1991_03
Patent number
US04997595

Reaction notes

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