Hydrazine hydrate (1:1) → HCID 178507274, compound

HRID 1400687Notes

Reaction equation

HRID 1400687 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.O.[NH2:14][NH2:15]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([NH2:11])[NH:15][N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27568393-(3-Bromophenyl)-3-oxopropanenitrile

Product 1

HCID 178507274HCID 178507274, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3-bromophenyl)-3-oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) in ethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentrated in vacuuo. Crude product was diluted with dichloromethane and stirred for 5 min. Solids were filtered and dried to afford 3-(3-bromophenyl)-1H-pyrazol-5-amine (30 g, 126 mmol, 81% yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.02 (br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J=1.6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.37-7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br. s., 0.8H). LCMS (M+H)=240.1.

Workup

  1. temperaturewas refluxed for 16 h
  2. temperatureMixture was then cooled
  3. concentrationconcentrated in vacuuo
  4. additionCrude product was diluted with dichloromethane
  5. filtrationSolids were filtered
  6. customdried

Sources & evidence

ORD record
ord-e452e712b1c047d19aaf68957e2f47ae
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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