Ethyl diazoacetate → HCID 178468627, compound

HRID 129829Notes

Reaction equation

HRID 129829 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].[N+:9](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-:10]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12]([C:11]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[NH:10][N:9]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 137268Ethynylpyridine

Product 1

HCID 178468627HCID 178468627, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-ethynylpyridine (10.3 g), ethyl diazoacetate (11.6 g), and toluene (100 ml) was stirred at 85° C. for 36 hours. The resulting mixture was rotavaped and the residue recrystallized with ethanol (50ml) to afford 9.81 g of 5-(2-pyridinyl)pyrazole-3-carboxylic acid ethyl ester as tan crystallines, mp 103°-105° C. NMR: 1.43 (t, 3H), 4.40 (q, 2H), 7.32 (s, 1H, 4-pyrazolyl H), 7.30, 7.78, 8.66 (3 m, 4H, pyridinyl H's).

Workup

  1. customthe residue recrystallized with ethanol (50ml)

Sources & evidence

ORD record
ord-f4be144e5e694420ac69094eac5b47d6
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Reaction notes

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