Hydrochloric Acid → 4,6-Dichloronicotinic acid

HRID 1161800Notes

Reaction equation

HRID 1161800 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][N:5]=[C:4]([Cl:12])[CH:3]=1.CO.[OH-].[Na+].Cl>C1COCC1.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]([Cl:12])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 2764083Methyl4,6-dichloronicotinate

Product 1

HCID 8171584,6-Dichloronicotinic acidYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4,6-dichloronicotinate in a mixture of THF (400 ml), MeOH (100 ml) and H2O (100 ml) was added a solution of NaOH (10 g) in 40 ml H2O. The mixture was stirred for 40 min. at room temp. Then, the solvents were reduced and it was acidified with conc. HCl to a pH of about 2. It was extracted using a mixture of Et2O/EtOAc and the organic layer was dried with Na2SO4. The solvents were removed and the residue dried in vacuo to obtain the title compound as a white solid (12.3 g, 69%). Rf (CHCl3/MeOH 10:1)=0.85. 1H-NMR (300 MHz, DMSO-D6): δ=8.80 (s, 1H), 7.90 (s, 1H).

Workup

  1. extractionIt was extracted
  2. additiona mixture of Et2O/EtOAc
  3. dry with materialthe organic layer was dried with Na2SO4
  4. customThe solvents were removed
  5. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-a8ea714c27754604a8e1efdf19e1cb26
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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