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

HRID 169

Reaction equation

HRID 169 reaction equation
COC(=O)C(C)(C)N.Cc1ccc(Cl)cc1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.Cc1ccccc1.[Na+].[Pd]>COC(=O)C(C)(C)Nc1ccc(C)cc1

Participants

7

Conditions

Temperature
120 °C

Procedure

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.

Sources & evidence

ORD record
ord-adf0259dd1b4403cabef49044d700c84
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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