Ammonium Hydroxide → HCID 178434626, compound

HRID 894115Notes

Reaction equation

HRID 894115 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([C:10]([O:12]CC)=O)[NH:4][N:3]=1.[OH-].[NH4+:16]>>[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([C:10]([NH2:16])=[O:12])[NH:4][N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 178470423HCID 178470423, compound

Product 1

HCID 178434626HCID 178434626, compoundYield 95.8%

Procedure

Ethyl 3-methyl-4-nitropyrazole-5-carboxylate (82.5 g, 0.41 mol) was heated at reflux in 600 ml of concentrated ammonium hydroxide for 2 hours. Concentrated ammonium hydroxide (100 ml) was added and the solution was heated at reflux for an additional three hours. The solution was concentrated in vacuo until the product began to crystallize. The crude material was recrystallized from 700 ml of water to give 47 g product, m.p. 218°-220° (decomp). From the mother liquor was recovered 25 g of 3-methyl-7-nitropyrazole-5-carboxylic acid. Based on the amount of nitro acid consumed, the yield was 95.8%.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for an additional three hours
  3. concentrationThe solution was concentrated in vacuo until the product
  4. customto crystallize
  5. customThe crude material was recrystallized from 700 ml of water

Sources & evidence

ORD record
ord-50632fea97cf44b78583d9397849f685
Source dataset
uspto-grants-1981_08
Patent number
US04282361

Reaction notes

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