Hydrazine hydrate (1:1) → HCID 178469841, compound

HRID 1287258Notes

Reaction equation

HRID 1287258 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:16]CCCC)=[C:8]([C:13](=O)[CH3:14])[C:9]([OH:12])=[N:10][CH:11]=1)=[O:5])[CH3:2].O.[NH2:22]N>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[NH:16][N:22]=[C:13]([CH3:14])[C:8]=2[C:9]([OH:12])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178448824HCID 178448824, compound

Product 1

HCID 178469841HCID 178469841, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.4 g. of 3-acetyl-4-butylamino-2-hydroxypyridine-5-carboxylic acid ethyl ester (0.03 mol.) are dissolved in 20 ml. of acetic acid, 3 ml. of hydrazine-hydrate are added and the mixture is refluxed for 5 hours. After this time, the solvent is removed in vacuo and the crystalline precipitate of 4-hydroxy-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester is recrystallized from acetic acid, yield 5.1 g. (77%), m.p. 310°.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. customAfter this time, the solvent is removed in vacuo
  3. customthe crystalline precipitate of 4-hydroxy-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester is recrystallized from acetic acid, yield 5.1 g

Sources & evidence

ORD record
ord-7f25cff992cc4cf48c506f27e60d5150
Source dataset
uspto-grants-1976_10
Patent number
US03984422

Reaction notes

Loading…