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

HRID 877605Notes

Reaction equation

HRID 877605 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-23bf90c206544520abe991139c5b451d
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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