Glycerol → HCID 3640834, compound

HRID 1991062Notes

Reaction equation

HRID 1991062 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([CH3:14])[CH:6]=1)(=O)[CH3:2].O[CH2:16]C(CO)O.OS(O)(=O)=O>>[CH3:14][C:7]1[CH:6]=[C:5]2[C:10]([CH:16]=[CH:2][CH:1]=[N:4]2)=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 27373784-Acetamido-2-methylnitrobenzene

Product 1

HCID 3640834HCID 3640834, compoundYield 34.4%

Procedure

4-Acetamido-2-methylnitrobenzene (4.5 g; 23.2 mmol) glycerol (9 g; 100 mmol), H2SO4 conc (6.75 g) and As2O5.5H2O (3.6 g; 46.4 mmol) were heated at 130° C. for 20 h. The reaction mixture was poured on water, adjusted to pH 7-8 by adding NH3conc. and extracted with EtOAc three times. The combined organic phases were dried over Na2SO4, evaporated and purified via chromatography (SiO2; TBME/hexanes 70/30) to yield the title compound (1.5 g; 34%). The isomeric 5-methyl-6-nitroquinoline was eluted from the column after the title compound (850 mg; 19%).

Workup

  1. additionThe reaction mixture was poured on water
  2. additionby adding NH3conc
  3. extractionand extracted with EtOAc three times
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated
  6. custompurified via chromatography (SiO2; TBME/hexanes 70/30)

Sources & evidence

ORD record
ord-50eb3d652f894a71a2efe09055562c23
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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