Cyclopentylhydrazine hydrochloride → 1-Cyclopentyl-3-methyl-1H-pyrazol-5-amine

HRID 1522421Notes

Reaction equation

HRID 1522421 reaction equation
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.N/[C:10](/[CH3:14])=[CH:11]\[C:12]#[N:13]>C(O)C>[CH:2]1([N:7]2[C:12]([NH2:13])=[CH:11][C:10]([CH3:14])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 5325263(2Z)-3-Amino-2-butenenitrile

Product 1

HCID 31525241-Cyclopentyl-3-methyl-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 19 using cyclopentylhydrazine hydrochloride (2 g, 14.64 mmol), (2Z)-3-amino-2-butenenitrile (1.202 g, 14.64 mmol) and ethanol (20 mL). The final product was collected as 0.57 g (24%). LCMS E-S (M+H)=166.0. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.60-1.69 (m, 2 H), 1.86-1.95 (m, 2 H), 1.99-2.09 (m, 4 H), 2.19 (s, 3 H), 3.46 (br. s., 2 H), 4.38 (quin, J=7.89 Hz, 1 H), 5.36 (s, 1 H).

Workup

  1. customThe final product was collected as 0.57 g (24%)

Sources & evidence

ORD record
ord-02c3a69aac73405e92c6ae558aee1d85
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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