Ammonia → 5-Nitroisoquinoline-4-carboxylic acid

HRID 972378Notes

Reaction equation

HRID 972378 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[N:11][CH:10]=1)([OH:8])=[O:7].N>S(=O)(=O)(O)O>[C:6]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N+:1]([O-:4])=[O:2])[CH:12]=[N:11][CH:10]=1)([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 459768Isoquinoline-4-carboxylic acid

Product 1

HCID 227500955-Nitroisoquinoline-4-carboxylic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A nitrating mixture obtained by dissolving potassium nitrate (94 g.) in concentrated sulphuric acid (d= 1.83) (750 cc.) is added dropwise, over the course of 1 hour, to a solution of 4-carboxy-isoquinoline (146.8 g.) in concentrated sulphuric acid (d= 1.83) (880 cc.). The solution obtained is kept at a temperature of about 20° C. for 16 hours and is then poured onto ice (18 kg.). Ammonia (11 N) (5.5 liters) is added gradually, whilst stirring and keeping the temperature of the mixture at between 15° and 20° C. The yellow precipitate which has appeared is filtered off, washed with water (800 cc. in total) and then dried. 4-Carboxy-5-nitro-isoquinoline (144 g.) melting at 285° is thus obtained.

Workup

  1. customA nitrating mixture obtained
  2. customThe solution obtained
  3. additionis then poured onto ice (18 kg.)
  4. customat between 15° and 20° C
  5. filtrationThe yellow precipitate which has appeared is filtered off
  6. washwashed with water (800 cc. in total)
  7. customdried

Sources & evidence

ORD record
ord-559df437f59e40f0b9bc927c367b7cc1
Source dataset
uspto-grants-1977_10
Patent number
US04053300

Reaction notes

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