Dimethylformamide → HCID 178469847, compound

HRID 1287259Notes

Reaction equation

HRID 1287259 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[NH:15][N:14]=[C:13]([CH3:16])[C:8]=2[C:9]([OH:12])=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24].CN(C)C=O>O.C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[NH:15][N:14]=[C:13]([CH3:16])[C:8]=2[C:9]([O:12][CH2:23][CH3:24])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469841HCID 178469841, compound

Product 1

HCID 178469847HCID 178469847, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2.2g. of 4-hydroxy-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester (0.01 mol.), 2.8 g. of potassium carbonate (0.02 mol.), and 1.6 g. of ethyl iodide (0.01 mol.) are suspended in 50 ml. of dimethylformamide and heated for 10 hours at 70°. After this time, the mixture is acidified with acetic acid and 30 ml. of water are added. 4-Ethoxy-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester precipitates, is filtered and recrystallized from methanol, yield 1.9 g. (79%), m.p. 200°.

Workup

  1. custom4-Ethoxy-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester precipitates
  2. filtrationis filtered
  3. customrecrystallized from methanol, yield 1.9 g

Sources & evidence

ORD record
ord-b9a8690124a14d88910f92b70d320f83
Source dataset
uspto-grants-1976_10
Patent number
US03984422

Reaction notes

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