Hydrochloric Acid → (2-methyl-4-nitro-1H-indol-1-yl)acetic acid

HRID 505934Notes

Reaction equation

HRID 505934 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([CH3:21])[N:10]2[CH2:15][C:16]([O:18]CC)=[O:17])([O-:5])=[O:4].Cl>C(O)C>[CH3:21][C:9]1[N:10]([CH2:15][C:16]([OH:18])=[O:17])[C:11]2[C:7]([CH:8]=1)=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59431290HCID 59431290, compound

Product 1

HCID 59431292(2-methyl-4-nitro-1H-indol-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Aqueous sodium hydroxide (1 M, 25 ml) was added to a solution of (4-nitro-2-methyl-1H-indol-1-yl)acetic acid, ethyl ester (5.0 g, 18.9 mmol) in ethanol (25 ml) and the mixture warmed to 40° C. After stirring for 70 mins at this temperature, the mixture was allowed to cool back to ambient temperature and aqueous hydrochloric acid (1 M, 27.5 ml) added causing precipitation of a solid. This was collected by filtration, washed with water (2×25 ml) then dried in a vacuum oven at 50° C. overnight to leave (2-methyl-4-nitro-1H-indol-1-yl)acetic acid as a yellow solid, 4.18 g (94%).

Workup

  1. temperatureto cool back to ambient temperature
  2. customprecipitation of a solid
  3. filtrationThis was collected by filtration
  4. washwashed with water (2×25 ml)
  5. customthen dried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-14fcd721ee4642978498c392f690a890
Source dataset
uspto-grants-2010_08
Patent number
US07781598B2

Reaction notes

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