Ammonium Hydroxide → 5-Bromo-8-nitroisoquinoline

HRID 736436Notes

Reaction equation

HRID 736436 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2.[OH-].[NH4+]>S(=O)(=O)(O)O>[Br:6][C:7]1[CH:16]=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Product 1

HCID 8169835-Bromo-8-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of potassium nitrate (120 g, 1.2 mol) in conc. sulphuric acid (500 ml) was added to a mixture of 5-bromoisoquinoline (219.4 g, 1.05 mol) and conc. sulphuric acid (400 ml) at below 10° C. during 1.5 h. The reaction was poured out on ice (4 l) and was neutralised by addition of conc. ammonium hydroxide (2 l) and ice (4 l). The crystals were filtered and air dried. Yield 216.9 g (82%). Mp 129-130° C.

Workup

  1. additionThe reaction was poured out on ice (4 l)
  2. filtrationThe crystals were filtered
  3. customair dried

Sources & evidence

ORD record
ord-129cda52cc6643c9b09923bf072e8974
Source dataset
uspto-grants-2009_09
Patent number
US07595336B2

Reaction notes

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