Water → 2-(Methyl(4-nitrophenyl)amino)ethan-1-ol

HRID 1590531Notes

Reaction equation

HRID 1590531 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[N+:6]([C:9]1[CH:14]=[CH:13][C:12](F)=[CH:11][CH:10]=1)([O-:8])=[O:7].C([O-])([O-])=O.[K+].[K+].O>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CN(C)C=O>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:2]([CH2:3][CH2:4][OH:5])[CH3:1])=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 45470772-(Methyl(4-nitrophenyl)amino)ethan-1-olYield 74.5%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

5.25 g of N-methylethanolamine, 11.2 g of p-nitrofluorobenzene, 9.7 g of K2CO3 and 2 drops of tricaprylmethylammonium chloride in 70 ml of dimethylformamide were heated at 95° C. for 3 days. The resulting reaction mixture was poured onto 350 ml of water. The precipitated product was filtered off under suction, after which the aqueous phase was extracted with toluene. After drying and evaporating down the toluene solution, the two product fractions were combined and recrystallized from ethanol/water in a volume ratio of 2 1. 10.22 g of 2-[N-(p-nitrophenyl)-N-methylamino]-ethanol having the following physical properties were obtained: melting point: 99°-101° C., IR spectrum (KBr pellet): bands at 3,450, 2,900, 2,850, 1,690, 1,680, 2,900, 1,580, 1,470, 1,450, 1,330, 1,320, 1,110, 1,060 and 825 cm-1 ; 1H nuclear magnetic resonance spectrum (400 MHz, CDCl3, tetramethylsilane as internal standard, chemical shift δ (in ppm): 8.05 (doublet, 2H), 6.64 (doublet, 2H), 3.9 (triplet, 2H), 3.65 (triplet, 2H), 3.15 (singlet, 3H) 2.02 (singlet, 1H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe precipitated product was filtered off under suction
  3. extractionafter which the aqueous phase was extracted with toluene
  4. customAfter drying
  5. customevaporating down the toluene solution
  6. customrecrystallized from ethanol/water in a volume ratio of 2 1

Sources & evidence

ORD record
ord-a51df1650d5d4e458d9999b790975de3
Source dataset
uspto-grants-1993_04
Patent number
US05204178

Reaction notes

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