4-Nitroaniline → HCID 136025189, compound

HRID 1376716Notes

Reaction equation

HRID 1376716 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:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1)[CH2:24][CH:25]=[CH2:26])[CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>Cl.O.C(O)(=O)C>[CH2:20]([N:23]([CH2:24][CH:25]=[CH2:26])[C:27]1[CH:32]=[CH:31][C:30]([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:29]([OH:33])[CH:28]=1)[CH:21]=[CH2:22]

Participants

9

Reactant 5

HCID 74754-NitroanilineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite2×HCID 44178882HCID 44178882, compound

Product 1

HCID 136025189HCID 136025189, compoundYield 87.2%

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-nitro aniline in 24 ml 5N HCl and 6 ml of distilled water. The suspension was cooled to 0° C. in an ice bath and 1.6 g of NaNO2 dissolved in 5 ml of 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 were combined 12 g sodium acetate, 24 ml of acetic acid and 4.5 g of the 3-(N,N-diallylamino)phenol, and the beaker was cooled to ca. 0° C. The contents of the first beaker were added to the second beaker slowly with stirring. After 2 hours, the mixture was 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 6.4 g of N,N-diallyl-4-(4'-nitrophenylazo)-3-hydroxyaniline.

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 ca. 0° C
  4. additionThe contents of the first beaker were added to the second beaker slowly
  5. stirringwith stirring
  6. waitAfter 2 hours
  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-a387bac0575548deb612e96f70d3ef14
Source dataset
uspto-grants-1997_09
Patent number
US05663308

Reaction notes

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