Methylhydrazine → HCID 86672048, compound

HRID 402472Notes

Reaction equation

HRID 402472 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=[C:4]([Cl:16])[N:3]=1.[CH3:17][NH:18][NH2:19]>CO>[Cl:16][C:4]1[N:3]=[C:2]2[N:18]([CH3:17])[N:19]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]2=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 14091939HCID 14091939, compound

Product 1

HCID 86672048HCID 86672048, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2,6-dichloropyridin-3-yl)(phenyl)methanone (0.7 g, 2.776 mmol) and methyl hydrazine (0.256 g, 5.553) in methanol (7 mL) was heated at 90° C. in a sealed tube for 4 h. The reaction mixture was concentrated under reduced pressure and diethyl ether was added. The organic layer was washed with an excess of water, followed by brine and dried over Na2SO4. Concentration of the organic layer furnished the crude product as a pale yellow solid. The product was purified by column chromatography (5% EtOAc in hexane) to yield the title compound (0.455 g, 68%) as a white solid. [1H-NMR (CDCl3, 300 MHz) δ 8.26 (d, 2H), 7.91 (m, 2H), 7.56-7.39 (m, 3H), 7.18 (d, 1H), 4.18 (s, 3H); HPLC RtA=5.880 min. (97%); LCMS RtC=1.990 min; [M+H]+=244.0; Mp=94-96° C.]

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and diethyl ether
  2. additionwas added
  3. washThe organic layer was washed with an excess of water
  4. dry with materialdried over Na2SO4
  5. customConcentration of the organic layer furnished the crude product as a pale yellow solid
  6. customThe product was purified by column chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-c7440c0b74d74f7991765ba3fd2e8930
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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