Dichloromethane → 4-Propylpyridine-2-carboxylic acid

HRID 901452Notes

Reaction equation

HRID 901452 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1C1C=CC=CC=1)[CH2:2][CH3:3].ClCCl.CN(C)C(Cl)=O.[C:26](=O)([O-:28])[O-:27].[K+].[K+]>Cl>[CH2:1]([C:4]1[CH:5]=[CH:6][N:7]=[C:8]([C:26]([OH:28])=[O:27])[CH:9]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 18446436HCID 18446436, compound

Product 1

HCID 214132834-Propylpyridine-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 4-propyl-(3-phenyl)pyridine-N-Oxide (1 g, 4.69 mmol) in dichloromethane (10 mL) trimethylsilyl cyanide (1.3 mL, 10 mmol) and dimethylcarbamyl chloride (1 mL, 10 mmol) was added and stirred at room temperature for 24 hours. Aqueous potassium carbonate (10%, 10 mL) was added and extracted with dichloromethane (100 mL). The crude product obtained on removal of solvent was taken in hydrochloric acid (6N, 30 mL) and refluxed for 24 hours. Removal of acid followed by crystallization of the crude product from acetonitrile resulted in acid 10b (1 g, 86%): MS (ESPOS): 240 [M−1]; 1H NMR (300 MHz, CD3OD) δ 2.03-2.17 (m, 2), 2.74 (t, J=7.2, 2), 3.04 (t, J=7.8, 2), 7.16-7.38 (m, 5), 8.07 (d, J=4.2, 1), 8.40 (s, 1), 8.71 (d, J=5.7, 1).

Workup

  1. extractionextracted with dichloromethane (100 mL)
  2. customThe crude product obtained on removal of solvent
  3. temperaturerefluxed for 24 hours
  4. customRemoval of acid
  5. customfollowed by crystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-6bd11f85f1a64f4aa41b1e0e243d759d
Source dataset
uspto-grants-2008_04
Patent number
US07361743B2

Reaction notes

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