Sodium Nitrate → HCID 59129201, compound

HRID 1847773Notes

Reaction equation

HRID 1847773 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[N+:18]([O-])([O-:20])=[O:19].[Na+]>S(=O)(=O)(O)O>[CH3:17][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][C:6]([N+:18]([O-:20])=[O:19])=[CH:7][CH:8]=2)([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 53438556Ethyl 2-(1H-indol-2-yl)-2-methylpropanoate

Product 1

HCID 59129201HCID 59129201, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

Ethyl 2-(1H-indol-2-yl)-2-methylpropanoate (1.0 g, 4.3 mmol) was dissolved in concentrated sulfuric acid (6 mL) and cooled to −10° C. (salt/ice-mixture). A solution of sodium nitrate (370 mg, 4.33 mmol) in concentrated sulfuric acid (3 mL) was added dropwise over 30 min. Stirring was continued for another 30 min at −10° C. The mixture was poured into ice and the product was extracted with dichloromethane. 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-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (0.68 g, 57%).

Workup

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

Sources & evidence

ORD record
ord-117c9768930c44c9b9dea7fe4a38ecf6
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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