Hydrochloric Acid → HCID 178418525, compound

HRID 4795

Reaction equation

HRID 4795 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].[Br:13][O-].[Na+].BrBr.Cl>O>[Br:13][C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([OH:1])=[N:10][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 24408BromineHCID 23673712Sodium hypobromite2×HCID 178418543HCID 178418543, compound

Product 1

HCID 178418525HCID 178418525, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 10 g (0.07 mole) of 2-hydroxy-nicotinic acid in 16.8 g of 50% sodium hydroxide (0.21 mole) diluted with 25 ml of water was added 200 ml of sodium hypobromite solution prepared by adding 13.6 g (0.17 mole) of bromine to a solution of 20.16 g of 50% sodium hydroxide (0.25 mole) in 125 ml of water at 0° C. diluted to 400 ml. After 24 hrs of stirring at room temperature, another 100 ml portion of the above sodium hypobromite solution was added and the reaction solution was stirred for another 24 hr. The reaction solution was cooled in an ice bath and acidified carefully with 12N hydrochloric acid. Crystallization from isopropyl alcohol gave 9.7 g (63.5%) of product. A sample was further recrystallized from 95% ethanol, m.p. 245° C.

Workup

  1. customprepared
  2. additiondiluted to 400 ml
  3. stirringthe reaction solution was stirred for another 24 hr
  4. temperatureThe reaction solution was cooled in an ice bath
  5. customCrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-f3db1044f1d24b8cbe93aa3f0f632b1b
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Linked notes

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