Dimethylamine → HCID 54565315, compound

HRID 1195637Notes

Reaction equation

HRID 1195637 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH2:11]=O.[CH3:13][NH:14][CH3:15]>C(O)C>[CH3:13][N:14]([CH2:11][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1)[CH3:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 69472-Nitrophenol

Product 1

HCID 54565315HCID 54565315, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of o-nitrophenol (1.0g, 7.19 mmoles), 37% aqueous formalin solution (0.81 ml, 10.78 mmoles) and 25% aqueous dimethylamine solution (1.9 ml, 10.78 mmoles) in 25 ml absolute ethanol was refluxed overnight and the volatile components then removed on a rotary evaporator. The resulting residue was chromatographed on silica gel (silica Woelm® 32-63 μ from Universal Scientific Inc.) using 5% methanol in methylene chloride as the eluent. The first major yellow band to elute contained 0.3g (23% yield) of 4-dimethylaminomethyl-2-nitrophenol. The next yellow band to elute contained 0.3g (23% yield) of the isomeric product, 2-dimethylaminomethyl-5-nitrophenol. The bismannich product remained on the column. The same results were obtained by using N,N,N',N'-tetramethyldiaminomethane instead of the dimethylamine and formalin.

Workup

  1. temperaturewas refluxed overnight
  2. customthe volatile components then removed on a rotary evaporator
  3. customThe resulting residue was chromatographed on silica gel (silica Woelm® 32-63 μ from Universal Scientific Inc.)
  4. washThe first major yellow band to elute

Sources & evidence

ORD record
ord-6e9b51b6a77a4ebeb604f0edf6911a15
Source dataset
uspto-grants-1992_05
Patent number
US05112739

Reaction notes

Loading…