Sodium Nitrate → ethyl 2-(5-nitro-1H-indol-2-yl)propanoate

HRID 1908518Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[N+:17]([O-])([O-:19])=[O:18].[Na+]>S(=O)(=O)(O)O>[N+:17]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2]([CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3]2)([O-:19])=[O:18]

Participants

Conditions

Temperature: -10 °C

Procedure

Ethyl 2-(1H-indol-2-yl)propanoate (0.91 g, 4.2 mmol) was dissolved in concentrated sulfuric acid (3.9 mL) and cooled to −10° C. (salt/ice-mixture). A solution of sodium nitrate (0.36 g, 4.2 mmol) in concentrated sulfuric acid (7.8 mL) was added dropwise over 35 min. Stirring was continued for another 30 min at −10° C. The mixture was poured into ice and the product was extracted with ethyl acetate. The combined organic phases were washed with a small amount of sat. aq. sodium bicarbonate. The product was purified by column chromatography on silica gel (5-30% EtOAc in hexane) to give ethyl 2-(5-nitro-1H-indol-2-yl)propanoate (0.34 g, 31%).

Workup

additionThe mixture was poured into ice
extractionthe product was extracted with ethyl acetate
washThe combined organic phases were washed with a small amount of sat. aq. sodium bicarbonate
customThe product was purified by column chromatography on silica gel (5-30% EtOAc in hexane)

Sources & evidence

ORD record: ord-c75f9413b9534a79aed1e71b0c2a2c90
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598181B2

Reaction notes

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