4-Nitrobenzoic Acid → Ethyl 3-[methyl(4-nitrobenzoyl)amino]propanoate

HRID 1877278Notes

Reaction equation

HRID 1877278 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][NH:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH3:13][N:14]([C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 61794881Ethyl 3-[methyl(4-nitrobenzoyl)amino]propanoateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-nitrobenzoic acid (16.7 g), ethyl 3-(methylamino)propanoate (13.1 g), 1-hydroxybenzotriazole monohydrate (18.4 g), and N,N-dimethylformamide (200 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23.0 g), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (28.0 g, 100%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1af1bdf48064ef08536db92f3a9f383
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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