4770-23-4

Upstream product

• 550-44-7 N-methylphthalimide 
• 770-09-2 benzyltrimethylsilane 
• 108-88-3 toluene 
• 100-39-0 benzyl bromide 
• 103-82-2 phenylacetic acid 
• 3700-55-8 2-(2-hydroxypropyl)isoindoline-1,3-dione 
• 114-76-1 sodium phenylphyruvate 
• 139232-47-6 potassium L-3-phenyllactate 
• 4702-13-0 N-phthaloylglycine 
• 622-29-7 N-Benzylidenemethylamine 
• 708-14-5 phthalide-3-carboxylic acid 
• 13005-36-2 potassium phenylacetate 

Downstream Products

• 40523-35-1 (3E)-3-benzylidene-2-methylisoindolin-1-one 
• 40523-36-2 (Z)-3-benzylidene-2-methyl-2,3-dihydro-1H-isoindolin-1-one 
• 32003-14-8 4-benzyl-2H-phthalazin-1-one 

Relevant academic research and scientific papers

The Dianion Derived from N-Methylphthalimide

Reduction of N-methylphthalimide with lithium in liquid ammonia provides a stable dianion which has been alkylated with various reagents.

DECARBOXYLATION OF PHTHALIDECARBOXYLIC ACIDS IN THE PRESENCE OF IMINES - A FACILE ROUTE TO ISOINDOLOBENZAZEPIN-5-ONES AND PHTHALIDEISOQUINOLINES

In aprotic solvents, or in the absence of any solvent, phthalidecarboxylic acids decarboxylate in the presence of imines at 130o to form 3-alkyl-3-hydroxyisoindolones or their dehydration products.In acetic anhydride as solvent the products obtained are acetylated aminoalkylphthalides.The reactions are used to synthesise isoindolobenzazepin-5-ones and phthalideisoquinoline alkaloids.

From conventional to microphotochemistry: Photodecarboxylation reactions involving phthalimides

A series of acetone-sensitized photodecarboxylation reactions involving phthalimides have been investigated using conventional and microphotochemistry. Both, intra- and intermolecular transformations were compared. In all cases examined, the reactions performed in microreactors were superior in terms of conversions or isolated yields. These findings unambiguously prove the advantage of microphotochemistry over conventional photochemical techniques.

Erratum: Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor (Aust. J. Chem. (2020) 73(12):1149-1157)

The authors wish to advise of errors in the above paper. In Table 3, footnote C should read 'Crude product contains 4-methylanisole or p-tolyl acetate.' In the left column of text on the same page as Table 3, the second last sentence should read 'When the para-substituted arylacetates 9b and 9c were employed, 4-methylanisole and p-tolyl acetate were detected by 1H NMR analysis of the crude reaction mixtures but no attempts were made to isolate these simple decarboxylation products.'

Intermolecular photodecarboxylation of electron-deficient substrates by phthalimides in water: Efficiency, selectivity and online monitoring

The intermolecular photodecarboxylation of arylacetic acids 3-5 in water by use of stoichiometric amounts of N-alkylated phthalimides 1a,b was investigated by NMR and online pH- and CO2-release sensing. Decreasing the electron donor capability of the arylacetic acids by 4-fluoro and trifluoromethyl substitution alters the efficiency of the photodecarboxylation and selectivity of the secondary reaction. A remarkable switch in reaction channel (A to B) was observed for perfluoropropionic acid.

Photodecarboxylative benzylations of phthalimides

Photoadditions of phenylacetates to phthalimides give the corresponding benzylated hydroxyphthalimidines in moderate to high yields of 29-90%. With 2-phenylpropanoate, photoaddition affords a diastereoisomeric mixture in a de of 24% in favour of the like-diastereoisomer. l-3-Phenyl lactate and 2-oxo-3-phenylpropanoate both furnish the benzylated product through subsequent loss of formaldehyde and decarbonylation, respectively.

Photodecarboxylative benzylation of N-alkylphthalimides: A concise route to the aristolactam skeleton

The photoinitiated metal-free benzylation of N-alkyl phthalimides with arylacetates in aqueous solution followed by acid-catalyzed dehydration serves as a convenient route to methoxy-substituted precursors to phenanthrene lactam alkaloids.

Synthesis of 4-Alkyl-1(2H)-phthalazinones and 4-Alkyl-2, 3-benzoxazin-1-ones via Ring Cleavage of 3-Substituted N-Alkylated-3-hydroxyisoindolin-1-ones

N-Alkyl (Me, Et, i-Pr, t-Bu)-substituted phthalimdes 5a-d were easily transformed to 1(2H)-phthalazinones 8d-i and 2,3-benzoxazin-1-ones 9d, f, and j via a one-pot addition-decyclization-cyclocondensation process.

The photodecarboxylative addition of carboxylates to phthalimides: Scope and limitations

Intermolecular photoinduced decarboxylative additions of a series of alkylcarboxylates to N-substituted phthalimides gave the corresponding hydroxyphthalimidines in moderate to high yields of 39-89%. The potassium salt of 1-adamantanecarboxylic acid predominately underwent simple decarboxylation when irradiated in the presence of N-methylphthalimide. In case of phthalimides carrying suitable leaving groups within the N-side chain, decarboxylation, retro-Aldol cleavage or decarbonylation preceded the intermolecular addition step.

Photodecarboxylative addition of carboxylates and ct-keto carboxylates to phthalimides

Intermolecular photoinduced decarboxylative additions of formate and a series of alkyl carboxylates as well as a-keto carboxylates to N-substituted phthalimides la-c and N-phthaloyl amino acid esters 3a-i gave hydroxy phthalimidines 2a-2j, 6a, b, 9 and hydroxy phthalimidine methyl esters 4a-4i in moderate to high yields. Only in one case (adamantane derivative 10) imide-catalyzed decarboxylation to give the corresponding hydrocarbon was observed. Thieme Stuttgart-.