p-Toluenesulfonic acid → 5-Morpholino-2-nitrobenzaldehyde

HRID 1487193Notes

Reaction equation

HRID 1487193 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>CC(C)=O.O>[O:18]1[CH2:19][CH2:20][N:15]([C:8]2[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:6]([CH:7]=2)[CH:2]=[O:1])[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 866996844-(3-(1,3-Dioxolan-2-yl)-4-nitrophenyl)morpholine

Product 1

HCID 37709635-Morpholino-2-nitrobenzaldehyde

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4-(3-(1,3-Dioxolan-2-yl)-4-nitrophenyl)morpholine (15.9 g, 56.7 mmol) was dissolved in a mixture of acetone and water (100 mL/100 mL). Then p-toluenesulfonic acid (2.0 g) was added and the mixture was heated to reflux for 4 hours. Ethyl acetate was added and the organic phase was washed with saturated sodium bicarbonate and brine, and then dried over anhydrous sodium sulfate, evaporated to afford the crude product 5-morpholino-2-nitrobenzaldehyde, which was used for the next step without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. washthe organic phase was washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-de63b71d6df4491989df949a82661622
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

Loading…