91639-92-8

Basic information

• Product Name: N-BUTYRYLINDOLINE
• Synonyms: N-BUTYRYLINDOLINE
• CAS NO: 91639-92-8
• Molecular Formula: C12H15NO
• Molecular Weight: 189.2536
• Mol File: 91639-92-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-BUTYRYLINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BUTYRYLINDOLINE(91639-92-8)
• EPA Substance Registry System: N-BUTYRYLINDOLINE(91639-92-8)

Safety Data

• Hazardous Substances Data: 91639-92-8(Hazardous Substances Data)

Upstream product

• 496-15-1 1-indoline 
• 141-75-3 butyryl chloride 
• 5339-85-5 2-aminophenethyl alcohol 
• 107-92-6 butyric acid 

Downstream Products

• 1119450-42-8 2-bromo-1-(indolin-1-yl)butan-1-one 
• 1612872-81-7 N-(1-butyrylindolin-7-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

A Chemoselective α-Oxytriflation Enables the Direct Asymmetric Arylation of Amides

Until recently, the direct oxidative oxysulfonylation of carbonyl compounds was limited to ketones. Here, we report the first direct oxytriflation of simple, non-activated amides. Amide umpolung with triflic anhydride and pyridine-N-oxide in the absence of external nucleophiles directly leads to the formation of reactive α-triflates in a single step, which provides a platform for the deployment of valuable downstream α-functionalization reactions. The utility of this method was demonstrated by in situ clean conversion to their corresponding bromides, as desirable starting materials for nickel-catalyzed deracemizing enantioselective arylation. This approach not only enables a telescoped asymmetric arylation of unsubstituted amides but also extends its scope because of the broad chemoselectivity and functional group tolerance of the method. Amides bearing a functional group in α-position are found in many natural products and drugs. The direct α-functionalization of amides is one of the most popular approaches to access these moieties. Classically, the α-functionalization of amides has been dominated by enolate chemistry; however, carboxamides are among the least C-H acidic carbonyl derivatives, and the presence of further carbonyl or carboxyl groups (such as esters and ketones) is therefore not usually tolerated. Here, we report the first direct α-oxytriflation of simple, non-activated amides using triflic anhydride and pyridine-N-oxide in the absence of external nucleophiles, which provides a platform for the deployment of valuable downstream α-functionalization reactions. The utility of this method was demonstrated by in situ clean conversion to the corresponding bromides, which are valuable starting materials for nickel-catalyzed deracemizing enantioselective arylation. A direct and chemoselective α-oxytriflation of simple and non-activated amides has been developed. This approach provides a platform for the development of valuable downstream α-functionalization reactions of amides. Furthermore, the combination of α-oxytriflation of amides and nickel-catalyzed Suzuki reaction provides an efficient approach for direct asymmetric α-arylation of simple amides.

Ruthenium-catalyzed C7 amidation of indoline C-H bonds with sulfonyl azides

A ruthenium-catalyzed direct C7 amidation of indoline C-H bonds with sulfonyl azides was developed. This procedure allows the synthesis of a variety of 7-amino-substituted indolines, which are useful in pharmaceutical. The good functional tolerances, as well as the mild conditions, are prominent feature of this method.

One-pot cyclization of 2-aminophenethyl alcohols: A novel and direct approach to the synthesis of N-acyl indolines

(Chemical Equation Presented) A unique one-pot cyclization of 2-aminophenethyl alcohols with carboxylic acids in the presence of PPh 3, CCL4, and NEt3 furnished the formation of N-acyl indolines in good to excellent yields. This new approach provides an efficient, scalable, low-cost, and direct access to the biologically important indolines which are further oxidizable to indoles and oxindoles.