Hydrochloric Acid → 2-Amino-N-(2-hydroxyethyl)benzamide

HRID 1864041Notes

Reaction equation

HRID 1864041 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[CH2:13]([CH2:15][NH2:16])[OH:14].Cl>O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:16][CH2:15][CH2:13][OH:14])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 8359Isatoic Anhydride

Product 1

HCID 30164842-Amino-N-(2-hydroxyethyl)benzamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round-bottomed flask was charged with isatoic anhydride (5.0 g, 0.030 mol) and 40 mL water. Ethanolamine (2.21 mL, 0.036 mol) was added slowly to the reaction mixture. The reaction mixture was acidified with 1N HCl and extracted with EtOAc. The aqueous layer was basified with 6N NaOH and extracted with EtOAc. The EtOac layer was dried over Na2SO4, filtered, and concentrated to dryness to afford 2-amino-N-(2-hydroxyethyl)benzamide (3.86 g, 70%).

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe EtOac layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4173bff4a4954617b3adcf05079719aa
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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