Diethylamine → HCID 178463879, compound

HRID 1287261Notes

Reaction equation

HRID 1287261 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[NH:15][N:14]=[C:13]([CH3:16])[C:8]=2[C:9](Cl)=[N:10][CH:11]=1)=[O:5])C.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18]>>[CH2:17]([N:19]([CH2:20][CH3:21])[C:9]1[C:8]2[C:13]([CH3:16])=[N:14][NH:15][C:7]=2[C:6]([C:4]([OH:3])=[O:5])=[CH:11][N:10]=1)[CH3:18]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 178469780HCID 178469780, compound

Product 1

HCID 178463879HCID 178463879, compound

Procedure

2.4 g. of 4-chloro-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester is refluxed with 20 ml. of diethylamine for 24 hours. The excess diethylamine is removed by distillation and the residue treated with 20 ml. of water. 4-Diethylamino-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester precipitates and is recrystallized from ethyl acetate. Yield 2.1 g. (76%), m.p. 85°-88°. Hydrolysis of this product with aqueous sodium hydroxide yields 4-diethylamino-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid.

Workup

  1. customThe excess diethylamine is removed by distillation
  2. additionthe residue treated with 20 ml
  3. custom4-Diethylamino-3-methyl-1H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester precipitates
  4. customis recrystallized from ethyl acetate
  5. customHydrolysis of this product with aqueous sodium hydroxide

Sources & evidence

ORD record
ord-cf2bd4912bbe4a1c91f144240c13fcbf
Source dataset
uspto-grants-1976_10
Patent number
US03984422

Reaction notes

Loading…