Hydrogen Peroxide → 2-Amino-5-ethylbenzoic acid

HRID 1725864Notes

Reaction equation

HRID 1725864 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8]C(=O)[C:6]2=[O:13])[CH3:2].[OH:14]O>[OH-].[Na+]>[NH2:8][C:9]1[CH:10]=[CH:11][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=1[C:6]([OH:13])=[O:14]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 5834875-ethyl-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 77444862-Amino-5-ethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of Example 1B (11.7 g, 66.9 mmol) in 1M NaOH (300 mL) was treated dropwise with 30% aqueous hydrogen peroxide (300 mL), heated to 50° C. for 30 minutes, cooled to room temperature, and filtered. The filtrate was adjusted to pH 4 with concentrated HCl, cooled to 4° C., and filtered. The filter cake was dried under vacuum to provide the desired product (4.46 g). MS (ESI(−)) m/e 164 (M−H)−.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. temperaturecooled to 4° C.
  4. filtrationfiltered
  5. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-179a8685d5bd48f68bc971d541887edd
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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