Nitric Acid → 6-Bromo-5-nitroquinoline

HRID 1890910Notes

Reaction equation

HRID 1890910 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N:12]([O-:14])=[O:13].[Na+].[N+]([O-])(O)=O.[OH-].[NH4+]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 792436-BromoquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 2805636-Bromo-5-nitroquinolineYield 2,325.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-bromoquinoline (2.0 g, 9.61 mmol) in concentrated sulfuric acid (10 mL) was cooled to 0° C. Sodium nitrite (27 mg, 0.384 mmol) was added, followed by dropwise addition of concentrated nitric acid (0.8 mL). The reaction mixture was stirred at 0° C. for 45 min. then at room temperature for 1 h, before pouring onto ice, resulting into a yellow precipitate. The mixture was neutralized to pH 7 with ammonium hydroxide. The precipitate was filtered, washed with water and dried in vacuo to yield 2.26 g of 6-bromo-5-nitro-quinoline as a light green solid (93% yield):): 1H NMR (CDCl3) δ 7.62 (dd, 1H), 7.94 (d, 1H), 8.07 (d, 1H), 8.17 (d, 1H), 9.06 (dd, 1H); MS (m/z) 253, 255 [M+H+]+.

Workup

  1. waitat room temperature for 1 h
  2. additionbefore pouring onto ice
  3. customresulting into a yellow precipitate
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-035fb0c0e0c943949e39518c8a6868fc
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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