Ethanol → Ethyl 3,4-Diaminobenzoate

HRID 1771112Notes

Reaction equation

HRID 1771112 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([NH2:11])=[C:2]([NH2:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 692633,4-Diaminobenzoic acid

Product 1

HCID 458855Ethyl 3,4-DiaminobenzoateYield 90.4%

Procedure

76 g of 3,4-diaminobenzoic acid (0.5 mol) and 300 mL anhydrous ethyl alcohol were added to a three-necked bottle, to which 6 mL concentrated sulphuric acid was added slowly under stirring at room temperature. After refluxing for 3 h, the reaction was completed. After concentration under reduced pressure, the residual solution was poured into ice water. The resulting mixture was adjusted to pH 7 with saturated sodium carbonate aqueous solution. After sucking filtration and drying, 81.5 g solid was obtained. Yield: 90.4%. MS: 181(M+1).

Workup

  1. additionwas added slowly
  2. temperatureAfter refluxing for 3 h
  3. concentrationAfter concentration under reduced pressure
  4. additionthe residual solution was poured into ice water
  5. filtrationfiltration
  6. customdrying

Sources & evidence

ORD record
ord-9cc707bf398b442a8953d9c5050c3c83
Source dataset
uspto-grants-2016_02
Patent number
US09249106B2

Reaction notes

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