Hydrazine → 3-(Morpholine-4-sulfonyl)aniline

HRID 1391551Notes

Reaction equation

HRID 1391551 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.NN>[Pd].C(O)C>[N:13]1([S:10]([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)(=[O:12])=[O:11])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 2374754-(3-Nitrophenylsulfonyl)morpholine

Product 1

HCID 5594103-(Morpholine-4-sulfonyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-Nitro-benzenesulfonyl)-morpholine (5.9 g, 21.7 mmol) was combined with 10% palladium on carbon (1 g), ethanol (60 mL), and hydrazine (5 mL) and heated at reflux for 18 h. The solution was filtered through celite, concentrated, and cooled to 0° C. Product precipitated out an colorless crystal (4.7 g, 89%). MS (ESI) m/z=243 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. filtrationThe solution was filtered through celite,
  4. concentrationconcentrated
  5. customProduct precipitated out an colorless crystal (4.7 g, 89%)

Sources & evidence

ORD record
ord-b08f1faa142846b09fe91bc68d0d6f65
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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