Hydrazine hydrate (1:1) → HCID 178507670, compound

HRID 475061Notes

Reaction equation

HRID 475061 reaction equation
O=[C:2]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]#[N:5].O.[NH2:16][NH2:17]>CCO>[C:9]1([C@@H:7]2[CH2:8][C@H:6]2[C:2]2[CH:3]=[C:4]([NH2:5])[NH:17][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86694682trans-3-Oxo-3-(2-phenylcyclopropyl)propanenitrile

Product 1

HCID 178507670HCID 178507670, compoundYield 127.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 39 (28.5 g, 153.87 mmol, 1.00 equiv) in EtOH (300 mL) under N2 was added 85% hydrazine hydrate (5.7 g, 100 mmol, 0.65 equiv), and the reaction mixture was stirred at 80° C. for 6 h. The reaction was cooled to RT, and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with DCM/MeOH gradient (1 to 5% MeOH) to afford 25.4 g (83%) of trans-3-(2-phenylcyclopropyl)-1H-pyrazol-5-amine (41) as a light yellow oil: 1H NMR (400 MHz, DMSO-d6): δ 7.30-7.10 (m, 5H), 5.15 (s, 1H), 4.90-4.20 (br s, 2H), 2.10-2.07 (m, 1H), 2.00-1.95 (m, 1H), 1.35-1.31 (m, 2H), 1H not seen; MS (ESI+) m/z=200 [M+1]+.

Workup

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by SiO2 chromatography
  4. washeluting with DCM/MeOH gradient (1 to 5% MeOH)

Sources & evidence

ORD record
ord-70fa2b952c454c8db3461ca02df539f2
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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