Sulfuric Acid → 5-Amino-8-quinolinecarboxamide

HRID 2281016Notes

Reaction equation

HRID 2281016 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.S(=O)(=O)(O)[OH:15].[OH-].[Na+]>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([NH2:13])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 218751195-Aminoquinoline-8-carbonitrile

Product 1

HCID 896472255-Amino-8-quinolinecarboxamideYield 99.6%

Conditions

Temperature
100 °C

Procedure

A reaction mixture of 5-amino-quinoline-8-carbonitrile (1000.00 mg; 4.29 mmol; 1.00 eq.) in sulfuric acid (5.00 ml; 93.80 mmol; 21.86 eq.) was stirred at 100° C. for 1 h. The reaction mixture was then cooled, poured into ice and neutralized with 2N sodium hydroxide to PH=9. The precipitate was filtered, washed with water and dried to afford 5-aminoquinoline-8-carboxamide (800 mg, yield 74.3%).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-042a044298b648de906a8a0ce7ff2507
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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