Water → 926236-16-0

HRID 57559Notes

Reaction equation

HRID 57559 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][CH:18]1[O:23][CH2:22][CH2:21][NH:20][CH2:19]1.O>CS(C)=O>[CH3:17][CH:18]1[CH2:19][N:20]([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH2:21][CH2:22][O:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 4106152-Methylmorpholine

Product 1

HCID 16775103926236-16-0

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 1-fluoro-4-nitrobenzene (5.64 g, 40.0 mmol) and potassium carbonate (11.1 g, 80.0 mmol) in DMSO (30 mL) was added 2-methylmorpholine (4.05 g, 40.0 mmol), then the mixture was heated at 100° C. for 4 hours. This solution was poured on to water (300 mL) and extracted with EA (3×100 mL). The combined organic phase was washed with brine and dried. Filtered and Pd/C (1.0 g) was added to the filtrate, charged with H2, and stirred at room temperature overnight. The catalyst was filtered and the filtrate was concentrated to give product as a light red solid. MS (m/z): 193 (M+H)+.

Workup

  1. extractionextracted with EA (3×100 mL)
  2. washThe combined organic phase was washed with brine
  3. customdried
  4. filtrationFiltered
  5. additionPd/C (1.0 g) was added to the filtrate
  6. additioncharged with H2
  7. filtrationThe catalyst was filtered
  8. concentrationthe filtrate was concentrated
  9. customto give product as a light red solid

Sources & evidence

ORD record
ord-274f18ee19604baab58089ba036b7bc9
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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