2-Methoxy-4-nitroaniline → HCID 53732734, compound

HRID 1904023Notes

Reaction equation

HRID 1904023 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[N:13]([O-])=O.[Na+].[C:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:30]=[CH:31][CH:32]=1)[N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][OH:27])(=[O:19])[CH3:18].C([O-])(=O)C.[Na+]>O.COCCO>[CH2:28]([N:24]([CH2:25][CH2:26][OH:27])[C:23]1[CH:30]=[CH:31][C:32]([N:13]=[N:5][C:4]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:3]=2[O:2][CH3:1])=[C:21]([NH:20][C:17](=[O:19])[CH3:18])[CH:22]=1)[CH3:29]

Participants

7

Reactant 4

HCID 73372-Methoxy-4-nitroanilineHCID 517045Sodium AcetateHCID 15333294N-{3-[Ethyl(2-hydroxyethyl)amino]phenyl}acetamideHCID 23668193Sodium Nitrite

Product 1

HCID 53732734HCID 53732734, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

8.3 g of 2-methoxy-4-nitroaniline was diazotized in a conventional manner using 4 g of sodium nitrite. The diazotized solution thus obtained was added to a mixture composed of 12 g of 3-acetylamino-N-ethyl-N-hydroxyethylaniline, 20 g of sodium acetate, 70 ml of methyl Cellosolve and 50 ml of water at a temperature of not more than 10° C. The mixture was stirred at a temperature range between 10° C. and 15° C. for 30 minutes, the crystals thus deposited were collected by filtration and washed with water. The crude product was recrystallized from acetonitrile to obtain 16 g of Compound [1-g].

Workup

  1. customThe diazotized solution thus obtained
  2. additionwas added to a mixture
  3. filtrationthe crystals thus deposited were collected by filtration
  4. washwashed with water
  5. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c5883362d183459fbf3ceec237ddbd30
Source dataset
uspto-grants-1984_03
Patent number
US04439513

Reaction notes

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