Hydrochloric Acid → HCID 178524411, compound

HRID 901250Notes

Reaction equation

HRID 901250 reaction equation
[Cl:1][O-].[Na+].[OH:4][C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].S([O-])([O-])=O.[Na+].[Na+].Cl>[OH-].[Na+].O>[Cl:1][C:11]1[CH:12]=[N:13][C:5]([OH:4])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 23665760Sodium HypochloriteHCID 178418543HCID 178418543, compound

Product 1

HCID 178524411HCID 178524411, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium hypochlorite (14% available chlorine, 35 mL, 82.21 mmol) solution was added to a stirred solution of 2-hydroxynicotinic acid (7 g, 50.3 mmol) in 10% aqueous NaOH solution. The solution was stirred for 48 h at room temperature. An aqueous solution of sodium sulfite (3.150 g, 25 mmol) was added and further stirred for 30 min at room temperature. The solution was diluted by cold water and pH was adjusted to 2 by cold dilute HCl. The solids formed were filtered, washed by cold water and dried to yield 6.8 g (78%) of 5-chloro-2-hydroxy-nicotinic acid (70) as white solids. MP: 276° C.; 1H-NMR (DMSO-d6): δ 8.23 (d, J=2.8 Hz, 1H), 8.29 (d, J=2.8 Hz, 1H); EIMS: 174 (M+1).

Workup

  1. stirringfurther stirred for 30 min at room temperature
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by cold water
  5. customdried

Sources & evidence

ORD record
ord-3fc9a73bb919455e833495ef5b2c17d3
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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