Sodium Bicarbonate → 3-Hydroxy-6-n-propylpyridine

HRID 1422074Notes

Reaction equation

N[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1.N([O-])=[O:12].[Na+].C(=O)([O-])O.[Na+]>Cl.O>[OH:12][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Amino-2-n-propylpyridine (70.3 g, 516 mmol) was dissolved in 1300 ml of 1M hydrochloric acid and sodium nitrite (35.6 g, 516 mmol) dissolved in 300 ml of water was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1/2 hour, heated to 70° C. for 2 hours, and then stirred at room temperature the overnight. The reaction mixture was neutralised to pH=8 by adding solid sodium hydrogen carbonate, and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography over silica gel 60, using ethyl acetate:petroleum ether (1:1) as the eluent. This gave 65.7 g (92%) of 5-hydroxy-2-n-propylpyridine as an orange wax. 1H-NMR (CDCl3, 200 MHz) δ: 0.91 (t, 3H); 1.68 (sext, 2H); 2.71 (t, 2H); 7.09 (d, 1H); 7.25 (dd, 1H); 8.13 (d, 1H); 11.79 (s, 1H).

Workup

additionwas added dropwise at 0° C
temperatureheated to 70° C. for 2 hours
stirringstirred at room temperature the overnight
extractionthe product was extracted into ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
customthe solvent was evaporated
customThe crude product was purified by column chromatography over silica gel 60

Sources & evidence

ORD record: ord-f8a9327ff9924cd7b4ce6b2894b420f3
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080754

Reaction notes

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