4-Nitroaniline → HCID 136035682, compound

HRID 1376712Notes

Reaction equation

HRID 1376712 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:11]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH2:20]([N:23]([C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1)[CH3:24])[CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>Cl.O.C(O)(=O)C>[CH2:20]([N:23]([CH3:24])[C:25]1[CH:30]=[CH:29][C:28]([N:11]=[N:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[C:27]([OH:31])[CH:26]=1)[CH:21]=[CH2:22]

Participants

9

Reactant 5

HCID 74754-NitroanilineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 19702682HCID 19702682, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 136035682HCID 136035682, compoundYield 101.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

In a small beaker was suspended 3.0 g (21.7 mmol) of p-nitroaniline in 20 ml 5N HCl and 5 ml of distilled water. The suspension was cooled to 0° C. in an ice bath and 1.6 g of NaNO2 dissolved in 3 ml of distilled water was slowly added via a pipette over 15 minutes while the temperature of the suspension was kept under 4° C. When all the sodium nitrite had been added, the suspension was stirred for an additional 1 hour. In a separate beaker, was combined 10 g sodium acetate, 20 ml of acetic acid and 3.9 g (26.1 mmol) of 3-(N-allyl-N-methylamino)phenol and the beaker was cooled to 0° C. The contents of the first beaker were added to the second beaker slowly with stirring. After 45 minutes, the contents of the beaker were poured into 100 ml of ice water and saturated aqueous sodium bicarbonate solution was added until the foaming stopped. The red solid was filtered, washed with excess distilled water and dried in a vacuum desiccator overnight to yield 6.9 g of N-allyl-N-methyl-4-(4'-nitrophenylazo)-3-hydroxyaniline. Recrystallization from THF/ethanol yielded 3.5 g as maroon needles.

Workup

  1. additionwas slowly added via a pipette over 15 minutes while the temperature of the suspension
  2. customwas kept under 4° C
  3. temperaturethe beaker was cooled to 0° C
  4. additionThe contents of the first beaker were added to the second beaker slowly
  5. stirringwith stirring
  6. waitAfter 45 minutes
  7. additionwas added until the foaming
  8. filtrationThe red solid was filtered
  9. washwashed
  10. distillationwith excess distilled water
  11. customdried in a vacuum desiccator overnight

Sources & evidence

ORD record
ord-2255255d21bb41a69a93236edf031a96
Source dataset
uspto-grants-1997_09
Patent number
US05663308

Reaction notes

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