Hydrochloric Acid → 2-(4-Chlorophenyl)pyridine-3-carboxylic acid

HRID 1058319Notes

Reaction equation

HRID 1058319 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15318002Methyl 2-(4-chlorophenyl)nicotinate

Product 1

HCID 136013732-(4-Chlorophenyl)pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing methyl 2-(4-chlorophenyl)nicotinate from the previous step (6.0 g, 24.2 mmol) in methyl alcohol (30 mL) was added 1N sodium hydroxide (29 mL). The mixture was stirred at room temperature overnight then neutralized with 1N hydrochloric acid (29 mL), evaporated in vacuo and dried overnight to yield the solid 2-(4-chlorophenyl)nicotinic acid (7.3 g, Theo. Yield=5.65 g, balance is NaCl; HPLC RT=2.17 min; LC-MS m/z=234).

Workup

  1. customevaporated in vacuo
  2. customdried overnight

Sources & evidence

ORD record
ord-e522d7fb69e74804a905a8e2baac2be9
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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