Nitric Acid → 5-Nitroisoquinoline-1-carboxylic acid

HRID 1181428Notes

Reaction equation

HRID 1181428 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[N+:14]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[C:1]2[C:11]([OH:13])=[O:12])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 68092Isoquinoline-1-carboxylic acid

Product 1

HCID 2856465-Nitroisoquinoline-1-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

Isoquinoline-1-carboxylic acid (3.98 g, 23.0 mmol) was dissolved in conc. sulfuric acid (16 ml) at 0° C. A mixture of conc. sulfuric acid (5 ml) and fuming nitric acid (5 ml) was added over 10 min. and the reaction stirred for a further 1 h at 0° C., then poured into ice-water (400 ml). The solid was collected by filtration, then washed with water (100 ml), ethanol (100 ml) and ether (100 ml), then dried under vacuum to give the title compound (4.1 g, 82%).

Workup

  1. additionwas added over 10 min.
  2. filtrationThe solid was collected by filtration
  3. washwashed with water (100 ml), ethanol (100 ml) and ether (100 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5a14113c17d045dfa70c11d5175d45d3
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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