Water → 3-Amino-6-chloroindazole-2-carboxylic acid dimethylamide

HRID 2072414Notes

Reaction equation

HRID 2072414 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[NH:10][N:9]=1.O>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:6])[C:3]([N:9]1[C:8]([NH2:7])=[C:16]2[C:11]([CH:12]=[C:13]([Cl:17])[CH:14]=[CH:15]2)=[N:10]1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 856286-chloro-1H-indazol-3-amine

Product 1

HCID 537093143-Amino-6-chloroindazole-2-carboxylic acid dimethylamideYield 58%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

0.15 mol of dimethylcarbamic acid chloride is added dropwise, while stirring, to 0.1 mol of 3-amino-6-chloroindazole in 50 ml of pyridine, in the course of which the temperature rises to 45° C. After 11/2 hours, 250 ml of water are allowed to run in and the reaction product is isolated by filtration. After dissolving the product in chloroform, filtering off a by-product of melting point 237°-238° C and evaporating the solution, 3-amino-6-chloroindazole-2-carboxylic acid dimethylamide (melting point: 178°-180° C; 58% of theory) is obtained.

Workup

  1. customrises to 45° C
  2. customis isolated by filtration
  3. filtrationfiltering off a by-product of melting point 237°-238° C
  4. customevaporating the solution

Sources & evidence

ORD record
ord-7eb222b11d5742848bae9745fa9996a3
Source dataset
uspto-grants-1977_09
Patent number
US04051252

Reaction notes

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