Nitric Acid → 1-Chloro-5-nitroisoquinoline

HRID 970667

Reaction equation

HRID 970667 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[N+:12]([O-])([OH:14])=[O:13].[N+]([O-])([O-])=O.[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 24434Potassium NitrateHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 4597741-Chloro-5-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1-chloroisoquinoline (6.0 g, 0.037 mol) in conc. H2SO4 (35 mL) was treated with a solution of fuming HNO3 (10 mL) and potassium nitrate (4.0 g, 0.040 mol) in conc. H2SO4 (35 mL) at 0-5° C. The mixture was stirred at 0° C. for a further 90 min, and poured into ice. The precipitate was collected, washed and dried to give the product as a yellow solid. LC-MS: 3.68 min, 209.2 & 211.1 (M+1).

Workup

  1. additionpoured into ice
  2. customThe precipitate was collected
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-b5ac563706ea427f81b60b2abccc3ca5
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Linked notes

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