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

HRID 1864120Notes

Reaction equation

HRID 1864120 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, 400MHz) 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-b46dda14bbc149679711a7ee94f04251
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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