Methylhydrazine → HCID 90417548, compound

HRID 1498879Notes

Reaction equation

HRID 1498879 reaction equation
[Br:1][C:2]1[C:3]([C:15]([O:17]CC)=O)=[C:4]([C:7](=O)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][CH:6]=1.[CH3:20][NH:21][NH2:22]>CCO>[Br:1][C:2]1[C:3]2[C:15](=[O:17])[N:21]([CH3:20])[N:22]=[C:7]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[C:4]=2[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 89539133HCID 89539133, compound

Product 1

HCID 90417548HCID 90417548, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of ethyl 4-bromo-2-isonicotinoylthiophene-3-carboxylate (5.2 g, 15.94 mmol) and methyl-hydrazine (2.2 g, 47.8 mmol) in EtOH (40 mL) was heated to reflux overnight. After removal of the solvent, the crude product was purified by silica gel column and eluted with 5:1 PE/EtOAc to give the title compound as a white solid (2.3 g, 44.8% yield). LC-MS (Method C): m/z 322 (M+H)+, Rt: 1.75 min. 1H NMR (400 MHz, DMSO-d6): δ=8.80-8.78 (m, 2H), 8.28 (s, 1H), 7.81-7.80 (m, 1H), 3.81 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customAfter removal of the solvent
  4. customthe crude product was purified by silica gel column
  5. washeluted with 5:1 PE/EtOAc

Sources & evidence

ORD record
ord-82c23012d0aa4d369224b84bc1101b10
Source dataset
uspto-grants-2015_12
Patent number
US09200005B2

Reaction notes

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