Hydrochloric Acid → 4-Pyridinecarboxylic acid, 2-chloro-6-(1,1-dimethylethyl)-

HRID 1055660Notes

Reaction equation

HRID 1055660 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([Cl:15])[N:14]=1)[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([Cl:15])[N:14]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86690963Methyl 2-chloro-6-(1,1-dimethylethyl)-4-pyridinecarboxylate

Product 1

HCID 438405834-Pyridinecarboxylic acid, 2-chloro-6-(1,1-dimethylethyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (4.39 mmol) of methyl 2-tert-butyl-6-chloroisonicotinate [lit.: O. Isler et al., Helvetica Chimica Acta 1955, 38 (4), 1033-1046] in 17 ml of THF and 8.8 ml (8.8 mmol) of 1 M aqueous sodium hydroxide solution were heated under reflux for 30 min. After cooling, the mixture was adjusted to pH 1 with concentrated hydrochloric acid and concentrated almost completely on a rotary evaporator. The solid formed was filtered off, washed with a little water and dried. This gave 870 mg (93% of theory) of the title compound.

Workup

  1. temperatureunder reflux for 30 min
  2. temperatureAfter cooling
  3. concentrationconcentrated almost completely on a rotary evaporator
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with a little water
  7. customdried

Sources & evidence

ORD record
ord-4dc74b5359744271a939bbe3cf4f0ce6
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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