Hydrochloric Acid → 4-PHENYLNICOTINIC ACID

HRID 1058320Notes

Reaction equation

HRID 1058320 reaction equation
[C:1]1([C:7]2[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:7]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12482255Methyl 4-phenylpyridine-3-carboxylate

Product 1

HCID 27629334-PHENYLNICOTINIC ACIDYield 132.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing methyl 4-phenylnicotinate (3.8 g, 17.8 mmol) from the previous step in methyl alcohol (20 mL) was added 1 N sodium hydroxide (21.4 mL). The mixture was stirred at room temperature for 6 hours, neutralized with 1 N hydrochloric acid, evaporated in vacuo and dried overnight to yield the solid 4-phenylnicotinic acid (4.7 g, Theo. Yield=3.6 g, balance is NaCl); HPLC RT=1.80 min, method A; LC-MS m/z=200; 1H NMR, 400 MHz, CD3OD, 8.91 ppm (s, 1H), 8.66 ppm (d, 1H), 7.48 ppm (d, 1H), 7.46-7.41 ppm (m, 5H).

Workup

  1. customevaporated in vacuo
  2. customdried overnight

Sources & evidence

ORD record
ord-983b7b848bbc4ad99f686872704b51b2
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

Loading…