(4-Nitrophenyl)acetic acid → 4-Di(2-hydroxyethyl)amino-4'-nitrostilbene

HRID 359572Notes

Reaction equation

HRID 359572 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([CH2:16][CH2:17][O:18]C(=O)C)[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)(=O)C.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31]C(O)=O)=[CH:27][CH:26]=1)([O-:24])=[O:23].N1CCCCC1>CN(C)C=O>[OH:18][CH2:17][CH2:16][N:7]([CH2:6][CH2:5][OH:4])[C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[CH:31][C:28]2[CH:29]=[CH:30][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 3287294-[Bis[2-(acetyloxy)ethyl]amino]benzaldehyde

Product 1

HCID 537015644-Di(2-hydroxyethyl)amino-4'-nitrostilbene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the crude reaction product of the previous step, viz. 4-di(2-acetyloxyethyl)aminobenzaldehyde, 270 g of 4-nitrophenyl acetic acid, 2 l of dimethyl formamide, and 100 ml of piperdine was stirred for 4 days at 20°-25° C. Next, the reaction mixture was concentrated by evaporation at 70° C. to a thick red oil, which was titrated three times, each time with 1 l of n-hexane. The residue was dissolved in 2.5 l of dimethyl formamide. Then there was added a solution of 320 g of sodium hydroxide in 800 ml of water. The resulting reaction mixture was then heated for 16 hours to 100° C. and subsequently poured into 10 l of ice water. The precipitated product was filtered off and thoroughly after-washed three times, each time with 1 l of water. After drying the crude reaction product was crystallized from 250 ml of dimethyl formamide and 500 ml of dichloromethane. The resulting yield of 4-di(2-hydroxy-ethyl) amino-4'-nitrostilbene was 190 g with a melting point of 184°-185° C. Calculated on N,N-di(2-hydroxyethyl)aniline this is 58% of theory.

Workup

  1. additionA mixture of the crude
  2. customreaction product of the previous step, viz
  3. concentrationNext, the reaction mixture was concentrated by evaporation at 70° C. to a thick red oil, which
  4. dissolutionThe residue was dissolved in 2.5 l of dimethyl formamide
  5. additionThen there was added a solution of 320 g of sodium hydroxide in 800 ml of water
  6. customThe resulting reaction mixture
  7. temperaturewas then heated for 16 hours to 100° C.
  8. filtrationThe precipitated product was filtered off
  9. washthoroughly after-washed three times
  10. customAfter drying the crude
  11. customreaction product
  12. customwas crystallized from 250 ml of dimethyl formamide and 500 ml of dichloromethane

Sources & evidence

ORD record
ord-1cd56a30055d412c92a4f61a50dad2c9
Source dataset
uspto-grants-1991_03
Patent number
US05001209

Reaction notes

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