Sodium ethoxide → Ethyl 4-ethoxypyrazolo[1,5-A]quinoxaline-3-carboxylate

HRID 65772Notes

Reaction equation

HRID 65772 reaction equation
Cl[C:2]1[C:3]2[N:4]([N:12]=[CH:13][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:20][CH2:21][O-:22].[Na+]>>[CH2:21]([O:22][C:2]1[C:3]2[N:4]([N:12]=[CH:13][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:20]

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 54256020Ethyl 4-chloropyrazolo[1,5-A]quinoxaline-3-carboxylate

Product 1

HCID 71390466Ethyl 4-ethoxypyrazolo[1,5-A]quinoxaline-3-carboxylate

Procedure

5.5 g. of 4-chloropyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester is heated for two hours with 10 ml. of a 2 molar sodium ethylate solution. The hot reaction solution is filtered and, upon cooling, 4-ethoxypyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester crystallizes in the form of white needles. The product is recrystallized from ethanol to obtain 3.4 g. of white crystals, m.p. 88°-90°.

Workup

  1. filtrationThe hot reaction solution is filtered
  2. temperatureupon cooling
  3. custom4-ethoxypyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester crystallizes in the form of white needles
  4. customThe product is recrystallized from ethanol
  5. customto obtain 3.4 g

Sources & evidence

ORD record
ord-6daf49346afc458aa34547c81e83efcf
Source dataset
uspto-grants-1978_12
Patent number
US04128716

Reaction notes

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