Hydrogen Bromide → HCID 67361836, compound

HRID 2091469Notes

Reaction equation

HRID 2091469 reaction equation
N[C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([I:12])=[CH:7]2.N([O-])=O.[Na+].[NH4+].[OH-].[BrH:21]>O>[Br:21][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([I:12])=[CH:7]2

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 14923Ammonium HydroxideHCID 23668193Sodium NitriteHCID 67363019HCID 67363019, compound

Product 1

HCID 67361836HCID 67361836, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 8-amino-3-iodo-6-methoxyquinoline (2.0 g) in HBr (20 ml) cooled to 0° C. is treated with a solution of sodium nitrite (0.48 g) in water (4 ml). The thick cold suspension is then added portionwise to a purple solution of CuBr2 (1.64 g) in 10 ml of conc. HBr preheated at 60° C. After 3 h an aqueous solution of NH4OH is added to the mixture to reach pH 14. After filtration of the mixture the filtrate is purified by flash chromatography (CH2Cl2) providing 8-bromo-3-iodo-6-methoxyquinoline (2.2 g) as a pale yellow solid. 1H NMR (CDCl3) δ ppm: 8.92 (1H, d); 8.32 (1H, d); 7.65 (1H, d); 6.82 (1H, d); 3.87 (3H, s).

Workup

  1. custompreheated at 60° C
  2. filtrationAfter filtration of the mixture the filtrate
  3. customis purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-4f430145668740418d6da8277ad89abd
Source dataset
uspto-grants-2013_05
Patent number
US08440595B2

Reaction notes

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