Hydrochloric Acid → HCID 59129178, compound

HRID 1404008Notes

Reaction equation

HRID 1404008 reaction equation
[CH3:1][C:2]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)([CH3:8])[C:3]([O:5]CC)=[O:4].O[Li].O.Cl>C1COCC1.O>[CH3:8][C:2]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59129201HCID 59129201, compound

Product 1

HCID 59129178HCID 59129178, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (4.60 g, 16.7 mmol) was dissolved in THF/water (2:1, 30 mL). LiOH.H2O (1.40 g, 33.3 mmol) was added and the mixture was stirred at 50° C. for 3 h. The mixture was made acidic by the careful addition of 3N HCl. The product was extracted with ethylacetate and the combined organic phases were washed with brine and dried over magnesium sulfate to give 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoic acid (4.15 g, 99%).

Workup

  1. extractionThe product was extracted with ethylacetate
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-0c75bec478b049b99e8575c384eb94a6
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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