19351-20-3

Usage

InChI:InChI=1/C12H17NO3/c1-4-13(5-2)12(15)9-7-6-8-10(16-3)11(9)14/h6-8,14H,4-5H2,1-3H3

Upstream product

• 62924-93-0 N,N-diethyl-3-methoxybenzamide 
• 85630-19-9 N,N-diethyl-1-carbamyloxy-2-methoxybenzene 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 530101-33-8 N,N-diethyl-2,3-dimethoxy-6-allylbenzamide 

Relevant academic research and scientific papers

Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation

A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues

The synthesis of several analogues of (±)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by

Directed ortho metalation of n,n-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri- and tetra-substituted oxygenated aromatics, phthalides and phthalic anhydrides

Full experimental details for the directed ortho metalation approch to a variety of simple ortho-substituted N,N-diethyl benzamides (Table 1) and contiguously 1,2,3- and 1,2,3,4-substituted benzamides (Tables 2) are given. The efficient conversion of these benzamides (6, 10, 12, 13, 18, 19) into phthalides (9a-b, 16b-c, 17) and phthalic anhydrides (8,16a), compounds previously available by demanding, classical methods, is detailed. A short synthesis of iso-ochracinic acid (27) is described.

The Directed Ortho Lithiation of O-Aryl Carbamates. An Anionic Equivalent of the Fries Rearrangement

Ortho-Lithiated O-aryl carbamates 3 constitute new synthetic intermediates which by treatment with a variety of electrophiles lead to ortho-substituted carbamates 4 and by rearrangement provide salicylamides 6.