Hydrazine → Methyl 4-hydrazinyl-3-(morpholinosulfonyl)benzoate

HRID 1777020Notes

Reaction equation

HRID 1777020 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].[NH2:21][NH2:22]>CO>[NH:21]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(=[O:14])=[O:13])[NH2:22]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 700043Methyl 4-fluoro-3-(morpholin-4-ylsulfonyl)benzoate

Product 1

HCID 71267396Methyl 4-hydrazinyl-3-(morpholinosulfonyl)benzoateYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 4-fluoro-3-(morpholinosulfonyl)benzoate (30 mg, 0.099 mmol) was added to hydrazine (4.44 mg, 0.138 mmol) in methanol (8 mL) and refluxed for 5 h at 65° C. The reaction was monitored by TLC. Upon completion of the reaction and cooling, the solvent was removed by vacuum, and the compound was purified by column chromatography affording the title compound (20 mg). 1H NMR (400 MHz, CD3OD): δ 8.15 (d, 1H, J=2.0 Hz), 8.03 (dd, 1H, J=2.4 & 9.2 Hz), 7.48 (d, 1H, J=9.2 Hz), 3.86 (s, 3H), 3.67 (m, 4H), 3.04 (m, 4H). ESI-MS: 316.1 [M+H]+.

Workup

  1. customUpon completion of the reaction
  2. temperaturecooling
  3. customthe solvent was removed by vacuum
  4. customthe compound was purified by column chromatography

Sources & evidence

ORD record
ord-a3aff6f309a7464e9dfa1b6565c143ff
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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