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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 590Generated: October 23, 2026

4-Bromobenzoic acid → 4-[(2-Carbamoylethyl)amino]benzoic acid

https://huagongshe.com/en/reaction/590

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Bromobenzoic acidHCID 11464—
Reactant3-Aminopropanamide hydrochlorideHCID 22222288—
ReagentLithium HexamethyldisilazideHCID 2733832—
CatalystPalladium (II) acetateHCID 4144353—
Catalyst(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-HCID 144543273—
SolventTetrahydrofuranHCID 8028—
Product4-[(2-Carbamoylethyl)amino]benzoic acidHCID 622313750%

Reaction Conditions

Temperature50 °C

Reaction Steps

Palladium (II) acetate (0.011 g, 0.05 mmol) was added to(R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (0.027 g, 0.05 mmol) in THF (1 mL) in a reaction vessel evacuated and purged with nitrogen. The resulting catalyst mixture was stirred and under nitrogen at 50 °C for 30 minutes. 04-Dec-2013 10:52:28 AM -0500 LiHMDS (1.194 mL, 1.19 mmol), 3-aminopropanamide, HCl (0.077 g, 0.62 mmol) and 4-bromobenzoic acid (0.1 g, 0.50 mmol) was added to a second reaction vessel and purged with nitrogen. were added at 20 °C. The catalyst solution was added to the reaction mixture and the resulting mixture was stirred at 120 °C for 16 hours. LCMS showed starting material only. Desired product not isolated from this reaction.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-f95171c2975240019dea4c87294370ec
Source note750 AstraZeneca ELN dataset