Ethanolamine → 4-amino-N-(2-hydroxyethyl)benzamide

HRID 381597Notes

Reaction equation

HRID 381597 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH2:11]([CH2:13][NH2:14])[OH:12].Cl.CN(C)CCCN=C=NCC.N=C=N>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:14][CH2:13][CH2:11][OH:12])=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 9784-Aminobenzoic AcidHCID 160435CarbodiimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 4587614-amino-N-(2-hydroxyethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-aminobenzoic acid (2.7 g, 20 mmol), ethanolamine (1.4 g, 23 mmol), and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (4.1 g, 21 mmol) in dimethylformamide (60 ml) was stirred overnight at room temperature. More carbodiimide (0.3 g, 2 mmol) was added and after stirring for one hour the reaction mixture was concentrated in vacuo onto silica gel (15 g). Purification by chromatography on silica gel (125 g) eluting with methanol:methylene chloride (3:97 to 1:19) and recrystallization from methanol:ethyl acetate gave, after drying under high vacuum, 4-amino-N-(2-hydroxyethyl)benzamide (1.65 g) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ: 3.26 (q, J=6 Hz, 2H, NCH2), 3.46 (q, J=6 Hz, 2H, OCH2), 4.68 (t, J=5.5, 1H, OH), 5.58 (br s, 2H, NH2), 6.51 (d, J=8.5 Hz, 2, Ar), 7.56 (d, J=8.5 Hz, 2H, Ar), 7.94 (br t, J=5.4 Hz, 1H, CONH). Mass spectrum (CI—CH4): 181 (M+1, 100%). Anal. Calculated for C912N2O2: C, 59.99; H, 6.71; N, 15.55. Found: C, 60.05; H, 6.72; N, 15.55.

Workup

  1. concentrationwas concentrated in vacuo onto silica gel (15 g)
  2. customPurification by chromatography on silica gel (125 g)
  3. washeluting with methanol:methylene chloride (3:97 to 1:19) and recrystallization from methanol
  4. customethyl acetate gave
  5. dry with materialafter drying under high vacuum, 4-amino-N-(2-hydroxyethyl)benzamide (1.65 g) as a white solid

Sources & evidence

ORD record
ord-7d77563eb4fc41da96c2c75af40bd531
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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