Hydrochloric Acid → HCID 178469848, compound

HRID 513287Notes

Reaction equation

HRID 513287 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([OH:13])[CH:3]=1.C1C(=O)N([Cl:21])C(=O)C1.Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[Cl:21][C:3]1[C:4]([OH:13])=[N:5][CH:6]=[C:7]([C:2]=1[OH:1])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 178469844HCID 178469844, compound

Product 1

HCID 178469848HCID 178469848, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4,6-dihydroxynicotinate (1.0 g, 5.43 mmol) in DMF (10 mL) was added NCS (797 mg, 5.96 mmol) and conc. HCl (0.05 mL). After stirring at room temperature for 2.5 h, it was added water and Na2S2O3, the precipitate was collected by filtration, washed with 1N HCl and dried to give ethyl 5-chloro-4,6-dihydroxynicotinate (920 mg).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with 1N HCl
  3. customdried

Sources & evidence

ORD record
ord-cade962f176d46f7bb417be6303cc58e
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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