Hydrochloric Acid → 4-(2'-Fluoro-5'-chlorobenzoyl)-5-hydroxynicotinic acid

HRID 234817Notes

Reaction equation

HRID 234817 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:3]=1[C:4]([C:6]1[C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=[CH:8][C:7]=1[OH:16])=[O:5].[OH-].[Na+].Cl>O.CO>[F:1][C:2]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:3]=1[C:4]([C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=[CH:8][C:7]=1[OH:16])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10710045Methyl 4-(2'-fluoro-5'-chlorobenzoyl)-5-hydroxynicotinate

Product 1

HCID 107326674-(2'-Fluoro-5'-chlorobenzoyl)-5-hydroxynicotinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-(2'-fluoro-5'-chlorobenzoyl)-5-hydroxynicotinate of Preparative Example 25 (1.2 g) is added to a solution of sodium hydroxide (0.67 g) in water (4 mL) and methanol (12 mL). A yellow solution is obtained after 5 min. The mixture is stirred at room temperature for 1.25 h. The resulting solution is acidified with 1N hydrochloric acid (14 mL) to pH=2 and the mixture is allowed to stand overnight. The white solid is collected by filtration and washed with water (3×5 mL) and dried to yield 4-(2'-fluoro-5'-chlorobenzoyl)-5-hydroxynicotinic acid (1.04 g).

Workup

  1. customA yellow solution is obtained after 5 min
  2. waitto stand overnight
  3. filtrationThe white solid is collected by filtration
  4. washwashed with water (3×5 mL)
  5. customdried

Sources & evidence

ORD record
ord-839816ea6edc4b5c95f50c5ae24b7b7b
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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