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

HRID 2090825Notes

Reaction equation

HRID 2090825 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].Cl.[CH2:14]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH2:20])[CH3:15].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:20][CH2:19][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:21])=[O:10])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 60643026Ethyl 3-[(4-nitrobenzoyl)amino]propanoateYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-nitrobenzoic acid (16.7 g), β-alanine ethyl ester hydrochloride (18.4 g), 1-hydroxybenzotriazol.monohydrate (18.4 g), triethylamine (16.7 mL) 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 a white solid. Recrystallization from ethyl acetate-hexane gave the title object compound (26.6 g, 100%) as white crystals.

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
  5. customto give a white solid
  6. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b66c61912a6d416d9664a4ad67c05b0a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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