Carbon Dioxide → HCID 18329802, compound

HRID 2271051Notes

Reaction equation

HRID 2271051 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].[O-]CC.[Na+].[CH2:14]([O:16][C:17](=[O:21])[CH:18]=[N+:19]=[N-:20])[CH3:15].C(=O)=O>C(O)C.O>[NH2:9][C:8]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:20][NH:19][C:18]=1[C:17]([O:16][CH2:14][CH3:15])=[O:21]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 12192Ethyl diazoacetateHCID 75959Pyridine-2-acetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 18329802HCID 18329802, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Pyridylacetonitrile (10 ml, 94.0 mmol) was added dropwise over 20 minutes to an ice-cooled solution of sodium ethoxide (34 ml, 2.76M, 94.0 mmol) in ethanol (50 ml), and the mixture stirred at 0° C. for 30 minutes. Ethyldiazoacetate (9.9 ml, 94.0 mmol) was added dropwise over 15 minutes and the reaction allowed to warm to room temperature and stirred for a furter 18 hours. Water (300 ml) was added, the mixture neutralised with solid carbon dioxide, and the resulting precipitate filtered and dried to afford the title compound, (13.0 g, 60%) as a brown solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for a furter 18 hours
  3. filtrationthe resulting precipitate filtered
  4. customdried

Sources & evidence

ORD record
ord-c88f7877d9fc4ae4bd1bab6f2bf99627
Source dataset
uspto-grants-2001_12
Patent number
US06333330B1

Reaction notes

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