Bromine → HCID 178418525, compound

HRID 1815887Notes

Reaction equation

HRID 1815887 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:11]Br>C(O)(=O)C>[Br:11][C:8]1[CH:9]=[N:10][C:2]([OH:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 178418543HCID 178418543, compound

Product 1

HCID 178418525HCID 178418525, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 5.0 g (35.9 mmol) of 2-hydroxy-nicotinic acid in 30 ml acetic acid was added dropwise 7.5 g (46.7 mmol) bromine. The mixture was maintained at 70-80° C. overnight. The mixture was cooled and the acetic acid was removed under reduced pressure. Water (100 ml) was added and the product was filtered and washed with water (3×100 ml). The solid was dried in a vacuum oven at 65° C. for 48 hours to provide 6.1 g (78% yield) of the title compound. MS: m/z (APCI, AP+) 219.0 [M.]+. CHN Analysis: Calcd: C, 33.06; H, 1.85; N, 6.42. Found: C, 32.91; H, 1.78; N, 6.23.

Workup

  1. temperatureThe mixture was cooled
  2. customthe acetic acid was removed under reduced pressure
  3. additionWater (100 ml) was added
  4. filtrationthe product was filtered
  5. washwashed with water (3×100 ml)
  6. customThe solid was dried in a vacuum oven at 65° C. for 48 hours

Sources & evidence

ORD record
ord-55eeab62b52247ba9bac5c1a45d6513f
Source dataset
uspto-grants-2005_04
Patent number
US06881743B2

Reaction notes

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