Ammonia → 5-Aminoquinoline-2-carboxylic acid amide

HRID 2054954Notes

Reaction equation

HRID 2054954 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:15])[N:6]=1)=O.[NH3:16]>>[NH2:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[CH:14][C:5]([C:3]([NH2:16])=[O:2])=[N:6]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 45089604Methyl 5-aminoquinoline-2-carboxylate

Product 1

HCID 692036145-Aminoquinoline-2-carboxylic acid amide

Conditions

Temperature
40 °C

Procedure

840 mg (4.16 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester is dissolved in 70 ml of a 7N methanolic ammonia solution. It is stirred for 3.5 hours at 40° C., then for 20 hours at room temperature. After the solvent is removed in a vacuum, the purification is carried out on silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-10%). 690 mg (88% of theory) of the product is obtained.

Workup

  1. waitfor 20 hours at room temperature
  2. customAfter the solvent is removed in a vacuum
  3. customthe purification
  4. custom690 mg (88% of theory) of the product is obtained

Sources & evidence

ORD record
ord-a1989b4824354b65ae801f37622e36cc
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

Loading…