Ethanol → Ethyl 3-aminobenzoate

HRID 1655589Notes

Reaction equation

HRID 1655589 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+].[CH2:22](O)[CH3:23]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:22][CH3:23])=[O:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74193-Aminobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 11400Ethyl 3-aminobenzoate

Procedure

To 3-aminobenzoic acid (7.00 g, 0.52 mol) dissolved in 300 mL of absolute ethanol was added ~3.5 mL of concentrated sulfuric acid. The reaction mixture was heated at reflux for 2 days and then cooled to ambient temperature. Potassium carbonate (8.9 g) was added and then most of the ethanol was removed under reduced pressure. The solution was partitioned between chloroform and water. The organic phase was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was filtered through silica gel eluting with ethyl acetate to afford the title compound. 1H NMR (CDCl3, 300 MHz) δ 1.40 (t, 3H), 3.85 (bs, 2H), 4.35 (q, 2H), 6.90 (m, 1H), 7.25 (m, 1H), 7.45 (m, 2H). MS (DCl/NH3) m/e 166 (M+H)+, 183 (M+H+NH3)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 days
  3. custommost of the ethanol was removed under reduced pressure
  4. customThe solution was partitioned between chloroform and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. filtrationwas filtered through silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-7325aa7c42d84219b0c77aa398ce56ab
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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