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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 169Generated: October 24, 2026

4-Chlorotoluene → Methyl 2-methyl-2-[(4-methylphenyl)amino]propanoate

https://huagongshe.com/reaction/169

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-ChlorotolueneHCID 7810—
ReactantMethyl 2-amino-2-methylpropanoateHCID 4186341—
ReagentSodium t-butoxideHCID 23676156—
CatalystPalladium (II) acetateHCID 4144353—
CatalystBis(adamantan-1-yl)(butyl)phosphaneHCID 11371790—
SolventTolueneHCID 1140—
ProductMethyl 2-methyl-2-[(4-methylphenyl)amino]propanoateHCID 609920310%

Reaction Conditions

Temperature120 °C

Reaction Steps

A flask was loaded with diacetoxypalladium (6.39 mg, 0.03 mmol), BUTYLDI-1-ADAMANTYLPHOSPHINE (0.020 g, 0.06 mmol), sodium 2-methylpropan-2-olate (0.164 g, 1.71 mmol) and methyl 2-amino-2-methylpropanoate (0.2 g, 1.71 mmol). The flask was evacuated and backfilled and toluene (5ml) and 1-chloro-4-methylbenzene (0.168 ml, 1.42 mmol) was added.The mixture was stirred for 20h at 120°. No conversion of startingmaterial was observed.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-adf0259dd1b4403cabef49044d700c84
Source note750 AstraZeneca ELN dataset