Hydroquinone → 3-(2-Hydroxy-4-nitrophenylamino)propionamide

HRID 131050Notes

Reaction equation

HRID 131050 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[C:12]([NH2:16])(=[O:15])[CH:13]=[CH2:14].C1(C=CC(O)=CC=1)O>S(=O)(=O)(O)O>[OH:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:1][CH2:14][CH2:13][C:12]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 6579AcrylamideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 231046323-(2-Hydroxy-4-nitrophenylamino)propionamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

15 g (0.1 mol) of 2-amino-5-nitrophenol, 7.8 g (0.11 mol) of acrylamide, 3 drops of 96% sulfuric acid and 20 mg of hydroquinone were maintained at 100° C. for 45 minutes. The mixture dissolved and an insoluble material was then formed, which was filtered off. This precipitate was taken up in 100 ml of refluxing toluene; after filtering while hot, 18 g of powder were obtained after re-slurrying in hot ethyl acetate (m.p.=194° C.).

Workup

  1. dissolutionThe mixture dissolved
  2. customan insoluble material was then formed
  3. filtrationwhich was filtered off
  4. filtrationafter filtering while hot, 18 g of powder
  5. customwere obtained after re-slurrying in hot ethyl acetate (m.p.=194° C.)

Sources & evidence

ORD record
ord-73092b98f9ef4017934e415ffcd94350
Source dataset
uspto-grants-2008_06
Patent number
US07384432B2

Reaction notes

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