Ethanolamine → 4-amino-N-(2-hydroxyethyl)-3-methoxybenzamide

HRID 529656Notes

Reaction equation

HRID 529656 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[NH2:32][CH2:33][CH2:34][OH:35]>C(Cl)Cl.C(O)(C)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:32][CH2:33][CH2:34][OH:35])=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

8

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 2880572486-69-3HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 537410594-amino-N-(2-hydroxyethyl)-3-methoxybenzamideYield 17%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-3-methoxybenzoic acid (1 equiv) in anhydrous DCM (0.6 M) was added triethylamine (4 equiv), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.2 equiv) and 2-amino-ethanol (2 equiv) portionwise. The mixture was stirred at room temperature overnight. After the reaction was complete, as monitored by LCMS, the mixture was diluted with a mixture of isopropanol in chloroform (30%), washed with water and dried over anhydrous sodium sulfate. The organic phase was concentrated and purified by silica column to give the title compound as a white solid (17% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.05-8.02 (t, J=5.6 Hz, 1H), 7.32-7.27 (m, 1H), 6.60 (d, J=8.0 Hz, 1H), 5.21 (brs, 2H), 4.69 (t, J=5.6 Hz, 1H), 3.80 (s, 3H), 3.50-3.46 (m, 2H), 2.34-3.27 (m, 2H). MS (ESI) m/z 211.1 [M+1]+.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organic phase was concentrated
  4. custompurified by silica column

Sources & evidence

ORD record
ord-81c3087424584a8090ef21efafa2b579
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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