Hydrazine → HCID 71258130, compound

HRID 877623Notes

Reaction equation

HRID 877623 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10](OC)=[O:11])(=[O:4])=[O:3].[NH2:15][NH2:16]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([NH:15][NH2:16])=[O:11])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 23436925HCID 23436925, compound

Product 1

HCID 71258130HCID 71258130, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 5-(methylsulfonyl)nicotinate (100 mg, 0.465 mmol) were added to hydrazine (17.87 mg, 0.558 mmol) in methanol (10 mL) and refluxed for 12 h at 70° C. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum and the compound was purified by flash column chromatography (3% CH3OH/CH2Cl2) afforded the title compound (83 mg, 80% yield) as a solid. 1H NMR (400 MHz, CDCl3): δ 9.20 (d, 1H, J=2.0 Hz), 9.17 (d, 1H, J=2.0 Hz), 8.61 (s, 1H), 3.11 (s, 3H). ESI-MS: 216.1 [M+H]+.

Workup

  1. customUpon completion of the reaction
  2. temperaturefollowing cooling
  3. customthe solvent was removed by vacuum
  4. customthe compound was purified by flash column chromatography (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-aada5f4f87514a9bbcde9e7ca66e519c
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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