Hydrochloric Acid → 1-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine

HRID 62522Notes

Reaction equation

HRID 62522 reaction equation
[CH2:1]([O:3][CH2:4][C:5](=O)[CH2:6][C:7]#[N:8])[CH3:2].C(O)(=O)C(O)=O.[CH2:16]([NH:18][NH2:19])[CH3:17].Cl>C(O)C>[CH2:16]([N:18]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:4][O:3][CH2:1][CH3:2])=[N:19]1)[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 575169104-Ethoxy-3-oxobutanenitrile

Product 1

HCID 575169111-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amineYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 25 mL round bottom was added 4-(ethyloxy)-3-oxobutanenitrile (550 mg, 4.33 mmol), ethyl hydrazine oxalate (641 mg, 4.33 mmol), and HCl (2.163 mL, 4.33 mmol) in ethanol (10 mL). The reaction mixture was stirred at the room temperature overnight. The reaction mixture was then evaporated, and partitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3. The organic layer was washed with brine, filtered and evaporated. 1-Ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-amine (420 mg, 2.234 mmol, 51.6% yield) was isolated as yellow oil. The product was used in the next step without further purification. LCMS (M+H)+=170.1 (M+H); 1H NMR (400 MHz, DMSO-d6) ppm 1.08 (t, J=6.95 Hz, 3 H) 1.19 (t, J=7.07 Hz, 3 H) 3.37-3.43 (m, 2 H) 3.81 (q, J=7.24 Hz, 2 H) 4.15 (s, 2 H) 5.09 (s, 2 H) 5.22 (s, 1 H).

Workup

  1. customThe reaction mixture was then evaporated
  2. custompartitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3
  3. washThe organic layer was washed with brine
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7385e4c7750341ceadf0ce305a7bca18
Source dataset
uspto-grants-2016_09
Patent number
US09446034B2

Reaction notes

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