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The first step is the formation of an enamine 2 using N,N-dimethylformamide dimethyl acetal and pyrrolidine. The desired indole 3 is then formed in a second step by reductive cyclisation. The Leimgruber-Batcho indole synthesis. In the above scheme, the reductive cyclisation is effected by Raney nickel and hydrazine.
Dimethylformamide, DMF is an organic compound with the chemical formula H C O N(CH 3) 2.Its structure is HC(=O)−N(−CH 3) 2.Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids.
Benzyl or tert-butyl acetoacetates also work well in this system, and with close temperature control, the tert-butyl system gives a very high yield (close to 80%). [10] N,N-dialkyl pyrrole-2- and/or 4-carboxamides may be prepared by the use of N,N-dialkyl acetoacetamides in the synthesis.
For this reason, acetonitrile and N,N-dimethylformamide are particularly commonly used. A typical Williamson reaction is conducted at 50 to 100 °C and is complete in 1 to 8 h. Often the complete disappearance of the starting material is difficult to achieve, and side reactions are common.
A large scale application of the Ritter reaction is in the synthesis of tert-octylamine, by way of the intermediate formamide.This process was originally described by Ritter in 1948, [11] and an estimated 10,000 tons/y (year: 2000) of this and related lipophilic amines are prepared in this way. [12]
Tert-butyl ethers (tBu) – Removed with anhydrous trifluoroacetic acid, hydrogen bromide in acetic acid, or 4 N hydrochloric acid [42] Allyl — Removed with potassium tert‑butoxide [43] DABCO in methanol, palladium on activated carbon, or diverse platinum complexes – conjoined with acid workup. [44]
n-Butyl acetate is an organic compound with the formula CH 3 CO 2 (CH 2) 3 CH 3. A colorless, flammable liquid, it is the ester derived from n- butanol and acetic acid . It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple.
In enzymology, a N,N-dimethylformamidase (EC 3.5.1.56) is an enzyme that catalyzes the chemical reaction N,N-dimethylformamide + H 2 O ⇌ {\displaystyle \rightleftharpoons } dimethylamine + formate Thus, the two substrates of this enzyme are N,N-dimethylformamide and H 2 O , whereas its two products are dimethylamine and formate .