Resorcinol → 4-(4-Methoxy-2-nitrophenylazo)benzene-1,3-diol

HRID 1737642Notes

Reaction equation

HRID 1737642 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[N:13]([O-])=O.[Na+].[C:17]1([CH:24]=[CH:23][CH:22]=[C:20]([OH:21])[CH:19]=1)[OH:18]>Cl.O.C(O)C>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([N:7]=[N:13][C:22]2[CH:23]=[CH:24][C:17]([OH:18])=[CH:19][C:20]=2[OH:21])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

7

Reactant 3

HCID 5054ResorcinolHCID 667934-Methoxy-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 1357039844-(4-Methoxy-2-nitrophenylazo)benzene-1,3-diolYield 74%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of diazonium salt, obtained beforehand by diazotization of 67.2 g (equivalent to 0.4 mol) of 4-methoxy-2-nitroaniline contained in 150 ml of concentrated HCl with a sodium nitrite solution containing 28 g (equivalent to 0.4 mol) in 100 ml of water at 0°-5° C., was added at a temperature of between 5° and 10° C. and over one hour into a reactor containing 44 g (equivalent to 0.4 mol) of resorcinol dissolved in a mixture of 400 ml of ethanol and 400 ml of water. The mixture was maintained under stirring for 2 hours. The red precipitate was filtered off and then rinsed copiously with water. 86 g (yield: 74%) of the desired compound was thereby obtained.

Workup

  1. additionwas added at a temperature of between 5° and 10° C. and over one hour into a reactor
  2. temperatureThe mixture was maintained
  3. filtrationThe red precipitate was filtered off
  4. washrinsed copiously with water

Sources & evidence

ORD record
ord-1c6ab801f9fc4d9ba2b724100eae52b4
Source dataset
uspto-grants-1999_10
Patent number
US05962484

Reaction notes

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