Methylhydrazine → HCID 66576808, compound

HRID 1525401Notes

Reaction equation

HRID 1525401 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[NH:14][N:15]=C(C3C=CC=CC=3)[C:3]=12.[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.[CH3:32]NN>>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH3:32])[N:15]=[C:27]([C:26]3[CH:25]=[C:24]([CH3:23])[CH:31]=[CH:30][CH:29]=3)[C:3]=12

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 121053-MethylbenzaldehydeHCID 86697018CID 86697018

Product 1

HCID 66576808HCID 66576808, compound

Procedure

Compound 19 was synthesised following similar procedures outlined in Example 22 (Compound 9), using 3-methylbenzaldehyde instead of benzaldehyde in Step 1 and methyl hydrazine instead of hydrazine hydrate in Step 3. As a slightly modified procedure, Step 3 was performed at 60° C. for 16 h in a sealed tube. Subsequently, the reaction mixture was partitioned between CH2Cl2 and water. The organic phase was separated using a phase separating cartridge and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, gradient 5 to 20% ethyl acetate/isohexane) yielding Compound 19 as a solid.

Workup

  1. customCompound 19 was synthesised
  2. customSubsequently, the reaction mixture was partitioned between CH2Cl2 and water
  3. customThe organic phase was separated
  4. customseparating cartridge
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography (silica gel, gradient 5 to 20% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-cbc7c17417224ab194903597e66d2757
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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