Hydrochloric Acid → Benzoic acid, 2-amino-4-ethyl-, ethyl ester

HRID 268495Notes

Reaction equation

HRID 268495 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH2:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8])[CH3:2].Cl.[CH2:14](O)[CH3:15]>>[NH2:12][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH2:14][CH3:15])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 138270842-Amino-4-ethylbenzoic acid

Product 1

HCID 21413817Benzoic acid, 2-amino-4-ethyl-, ethyl ester

Procedure

A mixture of 59.4 gm. of 4-ethylanthranilic acid and 1,000 cc. of ethanol is saturated with dry hydrogen chloride gas and then refluxed overnight. The reaction mixture is then concentrated in vacuo and the residue taken up between ether and sodium bicarbonate solution. The ether extract is dried and concentrated in vacuo to give ethyl 2-amino-4-ethylbenzoate as an oil (characterized by IR and NMR).

Workup

  1. additionA mixture of 59.4 gm
  2. temperaturerefluxed overnight
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. extractionThe ether extract
  5. customis dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d90bb7d2fa3d4b00be3a6035e279389c
Source dataset
uspto-grants-1976_03
Patent number
US03947582

Reaction notes

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