Hydrochloric Acid → 2-Amino-3-ethylbenzoic acid

HRID 2427072Notes

Reaction equation

HRID 2427072 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10]C(=O)[C:8]2=[O:13])[CH3:2].[OH-:14].[Na+].OO.Cl>>[NH2:10][C:11]1[C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:13])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2473657-ethyl-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 2260442-Amino-3-ethylbenzoic acid

Procedure

A mixture of 1.0 g of crude 7-ethyl-1H-indole-2,3-dione and 3 ml of a 2N aqueous sodium hydroxide solution was added dropwise to 2 g of aqueous hydrogen peroxide (30%) at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was adjusted to pH 4 by an addition of 2N hydrochloric acid, and a deposited precipitate was collected by filtration. The resulting filter cake was partitioned between ethyl acetate and a saturated sodium hydrogen carbonate solution. The aqueous layer was adjusted to pH 4 by an addition of 2N hydrochloric acid, and a deposited precipitate was collected by filtration to obtain 0.42 g of 2-amino-3-ethylbenzoic acid of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration
  2. filtrationThe resulting filter cake
  3. customwas partitioned between ethyl acetate
  4. additionThe aqueous layer was adjusted to pH 4 by an addition of 2N hydrochloric acid
  5. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-441b909dd81649cdafdf981225550670
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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