Hydrochloric Acid → 6-Methoxynicotinic acid

HRID 1663584Notes

Reaction equation

HRID 1663584 reaction equation
C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[OH-].[Na+].Cl.[CH2:14]([OH:16])C>>[CH3:14][O:16][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 1378606-Methylnicotinic acid

Product 1

HCID 5924996-Methoxynicotinic acid

Conditions

Temperature
60 °C

Procedure

To a solution of 6-methylnicotinic acid (35 mg) in ethanol (1 mL) was added 2N sodium hydroxide solution (0.14 mL) and the mixture was stirred at 60° C. for 2 hours. After cooling to room temperature, to the reaction mixture was added 5N HCl (0.06 mL) and the mixture was evaporated in vacuo to give 6-methyloxynicotinic acid. The product was treated in the same manner as described in Example 3 to give (3R)-1-[bis-(4-chlorophenyl)methyl]-3-[(6-methoxynicotinoyl)amino]pyrrolidine (28.0 mg; yield: 61%) as a powder.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. customthe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-259c05d757194b679be8d1c69279bbe3
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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