Hydrochloric Acid → 2-Amino-4-ethylbenzoic acid

HRID 978349Notes

Reaction equation

HRID 978349 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7](=[O:13])C(=O)[NH:9]2)=[CH:5][CH:4]=1)[CH3:2].[OH-:14].[Na+].OO.Cl>>[CH2:1]([C:3]1[CH:11]=[C:10]([NH2:9])[C:6](=[CH:5][CH:4]=1)[C:7]([OH:13])=[O:14])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 138270836-Ethyl-1H-indole-2,3-dione

Product 1

HCID 138270842-Amino-4-ethylbenzoic acid

Conditions

Temperature
50 °C

Procedure

In a 500 ml flask, was placed 16.84 gm of 6-ethyl isatin which was covered with 216 ml of 1.5M sodium hydroxide solution. With stirring, the mixture was warmed to 50° C. Heating was discontinued and the solution was treated with a 30% solution of hydrogen peroxide (24 ml) which was added at such a rate to maintain the temperature at between 50° to 65° C. The mixture was left to slowly cool to room temperature and was then acidified to pH 4 with concentrated hydrochloric acid. The precipitated product was then collected by filtration: mp. 117°-120° C.; yield 8.93 gm.

Workup

  1. customIn a 500 ml flask, was placed
  2. temperatureHeating
  3. additionwas added at such a rate
  4. temperatureto maintain the temperature at between 50° to 65° C
  5. waitThe mixture was left
  6. temperatureto slowly cool to room temperature
  7. filtrationThe precipitated product was then collected by filtration

Sources & evidence

ORD record
ord-36a80810a1724b698f3e85b59ff58f25
Source dataset
uspto-grants-1987_05
Patent number
US04665070

Reaction notes

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