Methylhydrazine → HCID 87304854, compound

HRID 401468Notes

Reaction equation

HRID 401468 reaction equation
[CH3:1][NH:2][NH2:3].[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([CH:19]=O)=[CH:17][N:18]=3)[CH:15]=2)[CH:5]=1.[CH2:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([NH:28][C:29]([N:2]([CH3:1])/[N:3]=[CH:19]/[C:16]1[N:14]2[CH:15]=[C:10]([C:6]3[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=3)[CH:11]=[CH:12][C:13]2=[N:18][CH:17]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 76639Benzyl isocyanateHCID 86670587HCID 86670587, compound

Product 1

HCID 87304854HCID 87304854, compoundYield 41%

Conditions

Temperature
85 °C

Procedure

Methyl hydrazine (41.25 mg, 0.8968 mmoles) was added to ethanolic solution of 6-(pyridin-3-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (100 mg, 0.4484 mmoles) at RT. The reaction mixture was heated at 85° C. for 1.5 hours. The solvent was then evaporated. The residue was dissolved in ethanol (5 ml), followed by addition of benzyl isocyanate (140.58 mg, 0.6726 mmoles). The reaction mixture was refluxed for 2 hours, then the solvent was evaporated. Water was poured into the residue and the aqueous solution was extracted with chloroform. Organic layer was separated, washed with water and brine and dried over sodium sulfate. The crude product was purified by column chromatography (100-200 mesh size silica gel, 1.5% methanol in chloroform). Yield: 41%; 1HNMR (DMSO-d6; 300 MHz): δ 9.48 (s, 1H), 9.05 (s, 1H), 8.58 (s, 1H), 8.21 (m, 3H), 7.98 (s, 1H), 7.80 (s, 2H), 7.29 (m, 6H), 4.39 (d, 2H, J=4.2 Hz), 3.35 (s, 3H); MS: m/z 384 (M+1)+.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionThe residue was dissolved in ethanol (5 ml)
  3. temperatureThe reaction mixture was refluxed for 2 hours
  4. customthe solvent was evaporated
  5. additionWater was poured into the residue
  6. extractionthe aqueous solution was extracted with chloroform
  7. customOrganic layer was separated
  8. washwashed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customThe crude product was purified by column chromatography (100-200 mesh size silica gel, 1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-a9f18c7d3892419d8dea61e9458e0fa7
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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