Hydrochloric Acid → 5-{[(Propan-2-yl)oxy]methyl}pyridine-2-carboxylic acid

HRID 1958392Notes

Reaction equation

HRID 1958392 reaction equation
[CH:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]#N)=[N:10][CH:11]=1)([CH3:3])[CH3:2].[OH-:14].[K+].[OH2:16].Cl>C(O)C>[CH:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:16])=[O:14])=[N:10][CH:11]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 218974155-{[(Propan-2-yl)oxy]methyl}pyridine-2-carbonitrile

Product 1

HCID 218974515-{[(Propan-2-yl)oxy]methyl}pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a 25 mL round-bottom flask was place ethanol (4 mL) solution of 5-isopropoxymethyl-pyridine-2-carbonitrile (1 g, 5.7 mmol). A solution of KOH (1.6 g, 28.36 mmol) in ethanol (6 mL) was added. The mixture was refluxed overnight and cooled down to room temperature. The resulted gel like mixture was added H2O and acidified with 6 mL of 10% HCl. The aqueous solution was extracted with EtOAc. The organic extracts were dried and concentrated to give the crude 5-isopropoxymethyl-pyridine-2-carboxylic acid. The crude product was further purified by column chromatography using 20% MeOH/CH2Cl2. 1H NMR (CDCl3, 400 MHz) δ 1.26 (d, 6H), 3.74 (m, 1H), 4.63 (s, 2H), 7.94 (d, 1H), 8.21 (m, 1H), 8.60 (s, 1H). Exact mass calculated for C10H13NO3 195.09, found 196.2 (MH+).

Workup

  1. customIn a 25 mL round-bottom flask was
  2. temperatureThe mixture was refluxed overnight
  3. extractionThe aqueous solution was extracted with EtOAc
  4. customThe organic extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be10dc49c34c45f1a7227761b1e66ad7
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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