Tetrahydrofuran → Ethyl 3-(4-aminobenzamido)propanoate

HRID 2090826Notes

Reaction equation

HRID 2090826 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[CH:6][CH:5]=1)([O-])=O.O1CCCC1>[C].[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 60643026Ethyl 3-[(4-nitrobenzoyl)amino]propanoate

Product 1

HCID 12469762Ethyl 3-(4-aminobenzamido)propanoateYield 95.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[(4-nitrobenzoyl)amino]propanoate (26.6 g) synthesized above, 5% palladium-carbon (8.9 g), tetrahydrofuran (150 mL) and ethanol (150 mL) was stirred at room temperature overnight under a hydrogen atmosphere. 5% Palladium-carbon was filtered off, and the filtrate was concentrated under reduced pressure to give a white solid. Recrystallization from ethyl acetate-diisopropyl ether gave the title object compound (22.6 g, 95%) as white crystals.

Workup

  1. filtration5% Palladium-carbon was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a white solid
  4. customRecrystallization from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-5e647a0f34d7472aadf26b2f56e4d3fe
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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