Methyl 5-hydroxypyridine-3-carboxylate → Methyl 6-chloro-5-hydroxynicotinate

HRID 2234218Notes

Reaction equation

HRID 2234218 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[N:6][CH:5]=1.[Cl:12][O-].[Na+]>Cl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([Cl:12])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 23665760Sodium Hypochlorite

Product 1

HCID 46941479Methyl 6-chloro-5-hydroxynicotinateYield 56%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a flask containing methyl-5-hydroxynicotinate (4.5 g, 29 mmol) was added sodium hypochlorite aqueous solution (6.15%, 26.7 mL, 22 mmol) dropwise under ice bath cooling. After 30 min of stirring, 2 M HCl (20 mL) was added and the resulting white crystals collected by filtration to give 2.31 g of 6-chloro-5-hydroxynicotinic acid methyl ester in 42% yield. 1H NMR (400 MHz, CDCl3) δ 10.32 (bs, 1H), 8.48 (d, 1H), 7.84 (d, 1H), 7.40 (s, 1H), 3.93 (s. 3H); LC-MS (ELSD): mass calcd for C7H6ClNO3 [M]+ 187. Found 187.

Workup

  1. temperaturecooling
  2. filtrationthe resulting white crystals collected by filtration

Sources & evidence

ORD record
ord-75fcee8ce0384b05b30a45b3cdcf7b4a
Source dataset
uspto-grants-2010_05
Patent number
US07709649B2

Reaction notes

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