Hydrochloric Acid → 4-[(3-Methoxypropyl)amino]-6-(1-methylethyl)pyridine-3-carboxylic acid

HRID 2192880Notes

Reaction equation

HRID 2192880 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[N:10]=[CH:9][C:8]=1[C:16]([O:18]CC)=[O:17].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:14])[CH3:15])[N:10]=[CH:9][C:8]=1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59625354Ethyl 4-[(3-methoxypropyl)amino]-6-(1-methylethyl)pyridine-3-carboxylate

Product 1

HCID 596256684-[(3-Methoxypropyl)amino]-6-(1-methylethyl)pyridine-3-carboxylic acidYield 126.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-[(3-methoxypropyl)amino]-6-(1-methylethyl)pyridine-3-carboxylate (263 mg) in ethanol (5 ml) was added 2 M aqueous sodium hydroxide solution (0.94 ml) and the mixture was stirred at room temperature for 15 hr. The reaction mixture was adjusted to pH 7 with 1 M hydrochloric acid, and the solvent was evaporated under reduced pressure. The residue was suspended in ethanol, and the precipitated inorganic salt was filtered off. The filtrate was concentrated under reduced pressure to give the object compound (300 mg) as a mixture of inorganic salts.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. filtrationthe precipitated inorganic salt was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-83ff2e2cb3d041feb2d1447d656acba3
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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