5-Nitro-3-isoquinolinecarboxylic acid → 5-Aminoisoquinoline-3-carboxylic acid

HRID 1902550Notes

Reaction equation

HRID 1902550 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:14]([OH:16])=[O:15])[N:8]=[CH:9]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([C:14]([OH:16])=[O:15])[N:8]=[CH:9]2

Participants

4

Reactant 1

HCID 193906095-Nitro-3-isoquinolinecarboxylic acid

Product 1

HCID 205156525-Aminoisoquinoline-3-carboxylic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Nitroisoquinoline-3-carboxylic acid (44 g) is dissolved in methanol (3 liters), and a catalyst consisting of palladium-on-carbon (3/97 by weight; 15 g) is added. The mixture is hydrogenated at atmospheric pressure, at a temperature between 20° and 25° C. After stirring for 5 hours, the volume of hydrogen absorbed is 13.9 liters. The mixture is filtered through diatomaceous silica and the filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 60° C. to yield 5-aminoisoquinoline-3-carboxylic acid (35 g).

Workup

  1. additionis added
  2. customis hydrogenated at atmospheric pressure, at a temperature between 20° and 25° C
  3. customthe volume of hydrogen absorbed
  4. filtrationThe mixture is filtered through diatomaceous silica
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 60° C.

Sources & evidence

ORD record
ord-f408aa0ee97740cc8926906d0cd84de3
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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