Hydrazine → HCID 178422686, compound

HRID 2093786Notes

Reaction equation

HRID 2093786 reaction equation
CC1C=C([N+]([O-])=O)C(C)=CC=1C(=O)C=C(N(C)C)C.NN.[CH3:22][C:23]1[CH:28]=[C:27]([N+:29]([O-])=O)[C:26]([CH3:32])=[CH:25][C:24]=1[C:33]1[NH:37][N:36]=[C:35]([CH3:38])[CH:34]=1>C(O)C.CO.[Pd]>[CH3:32][C:26]1[CH:25]=[C:24]([C:33]2[NH:37][N:36]=[C:35]([CH3:38])[CH:34]=2)[C:23]([CH3:22])=[CH:28][C:27]=1[NH2:29]

Participants

7

Reactant 3

HCID 9321HydrazineHCID 67170049HCID 67170049, compoundHCID 178422698HCID 178422698, compound

Product 1

HCID 178422686HCID 178422686, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2,5-dimethyl-4-nitrophenyl)-3-(dimethylamino)but-2-en-1-one (100 mg, 0.38 mmol) and hydrazine (60 uL, 1.9 mmol) in ethanol (3 mL) was heated in a microwave at 100° C. for 15 min. The obtained 5-(2,5-dimethyl-4-nitrophenyl)-3-methylpyrazol was dissolved in methanol (10 mL). To the solution was added Pd/C (10%). The reaction mixture was degassed and purged with H2 for several times and stirred under 1 atm. hydrogen gas overnight. The mixture was filtered and concentrated to afford 2,5-Dimethyl-4-(3-methyl-1H-pyrazol-5-yl)aniline. ESMS m/z 202 (M+H+).

Workup

  1. customThe reaction mixture was degassed
  2. custompurged with H2 for several times
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3eeb4a537b9461c9aa40d833f877fbe
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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