Ethyl Acetoacetate → HCID 21537672, compound

HRID 1076561Notes

Reaction equation

HRID 1076561 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][C:3]=1[N:9]=O.[Na].C([O:14][C:15](=[O:20])[CH2:16][C:17]([CH3:19])=O)C>C(O)C>[CH2:7]([N:6]1[C:2]2=[N:1][C:17]([CH3:19])=[C:16]([C:15]([OH:20])=[O:14])[N:9]=[C:3]2[CH:4]=[N:5]1)[CH3:8]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 353774HCID 353774, compoundHCID 5360545Sodium

Product 1

HCID 21537672HCID 21537672, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

49 g. of 5-amino-1-ethyl-4-nitrosopyrazole (0.35 mol.) are added to a solution of 8.05 g. of sodium (0.35 mol.) in 350 ml. of absolute ethanol and this is stirred at room temperature for 30 minutes. After the addition of 50 g. of acetoacetic acid ethyl ester (0.385 mol.) the reaction mixture is heated at reflux temperature for 31/2 hours. The precipitated sodium salt is filtered off, washed with ether and dried at 50°, yield 47.1 g. (59%). By dissolving the sodium salt in water, treatment with charcoal and acidification with concentrated hydrochloric acid, 1-ethyl-6-methyl-1H-pyrazolo-[3,4-b]pyrazine-5-carboxylic acid, m.p. 148°-149° (ethanol) is obtained.

Workup

  1. additionAfter the addition of 50 g
  2. temperatureat reflux temperature for 31/2 hours
  3. filtrationThe precipitated sodium salt is filtered off
  4. washwashed with ether
  5. customdried at 50°
  6. dissolutionBy dissolving the sodium salt in water, treatment with charcoal and acidification with concentrated hydrochloric acid, 1-ethyl-6-methyl-1H-pyrazolo-[3,4-b]pyrazine-5-carboxylic acid
  7. customm.p. 148°-149° (ethanol) is obtained

Sources & evidence

ORD record
ord-e3bcce2ebdb94a0aa16d7acae9baedad
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

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