2028-33-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved therapeutic properties and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, 2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione serves as a crucial building block for the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds enhances their effectiveness in controlling pests and weeds, thereby improving crop yields and quality.
Used in Organic Synthesis:
2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione is utilized as a versatile precursor in organic synthesis for the preparation of a wide range of chemical compounds. Its reactivity and structural features make it an ideal candidate for the synthesis of various organic molecules, including dyes, polymers, and other specialty chemicals.
Safety Precautions:
It is essential to handle 2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione with care, as it can be harmful if ingested or inhaled. Additionally, it may cause skin and eye irritation. Proper safety measures, such as wearing protective clothing and using appropriate ventilation, should be taken during its handling and use.

InChI:InChI=1/C12H11NO3/c1-7(8(2)14)13-11(15)9-5-3-4-6-10(9)12(13)16/h3-7H,1-2H3

Synthetic route

potassium phtalimide (1074-82-4) + 3-bromo-butanone (814-75-5) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
at 20℃; for 0.233333h; Ionic liquid;	96%
In N,N-dimethyl-formamide at 20℃;

3-chloro-2-butanone (4091-39-8) + potassium phtalimide (1074-82-4) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
In N,N-dimethyl-formamide at 20 - 25℃; for 8h; Temperature;	95%
In N,N-dimethyl-formamide at 20℃;
In N,N-dimethyl-formamide at 20℃; for 3h;
In N,N-dimethyl-formamide at 20℃;

2-(2-hydroxy-1-methyl-propyl)-isoindole-1,3-dione → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
With manganese(IV) oxide; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2,6-Di-tert-butyl-1,4-benzoquinone In acetone at 65℃; for 17h; Temperature; Inert atmosphere;	80%

2-(1-methylallyl)isoindole-1,3-dione (7065-05-6) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) + 2-(1,3-dioxoisoindolin-2-yl)butan-4-al (4667-80-5)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; nitromethane; oxygen; tert-butyl alcohol at 20℃; under 760.051 Torr; for 6h; Wacker Oxidation;	A n/a B 79%

methyllithium (917-54-4) + 2-phthalimidopropionic acid (21860-84-4) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -70 - 20℃; for 1h; Temperature;	62%

N-acetonylphthalimide (3416-57-7) + methyl iodide (74-88-4) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide at 60℃; for 17h;

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → 3-Amino-2-butanone hydrochloride (21419-24-9)

Conditions	Yield
With hydrogenchloride In acetic acid Heating;

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → 2-hydroxymethyl-N-(2-hydroxy-1-methylpropyl)-benzamide

Conditions	Yield
With sodium borohydrid In aqueous propan-2-ol; water; acetic acid

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → D,L-1-bromo-3-phthalimido-2-butanone (70386-38-8)

Conditions	Yield
With bromine In water; acetic acid at 20℃;
With bromine; acetic acid at 20℃;

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C21H16N4O2S (1240790-62-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine; acetic acid / 20 °C 2.1: ethanol / 20 °C 2.2: Reflux 3.1: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C21H20N4O6S (1240790-63-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine; acetic acid / 20 °C 2.1: ethanol / 20 °C 2.2: Reflux 3.1: Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H15N5O2S (1240790-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C13H11N3O2S (1240790-65-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C19H15N3O2S (1240790-66-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C15H13N3O3S

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H15N3O3S

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H17N3O2S (1240790-69-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C25H19N3O2S (1240790-70-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H16N4O2S (1240790-71-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C19H15N5O2S (1240790-72-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C22H15NO3 (1240790-59-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine; acetic acid / 20 °C 2.1: potassium carbonate / acetone / Reflux 2.2: Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C23H21NO7 (1240790-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: potassium carbonate / acetone / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C17H13N3O2 (1240790-61-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / butan-1-ol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → BrH*C13H12N4O2S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine; acetic acid / 20 °C 2.1: ethanol / 20 °C 2.2: Reflux View Scheme

Upstream product

• 1074-82-4 potassium phtalimide 
• 814-75-5 3-bromo-butanone 
• 53701-47-6 2-(1,3-dioxoisoindolin-2-yl)propanoyl chloride 
• 7065-05-6 2-(1-methylallyl)isoindole-1,3-dione 
• 917-54-4 methyllithium 
• 21860-84-4 2-phthalimidopropionic acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 4091-39-8 3-chloro-2-butanone 
• 3416-57-7 N-acetonylphthalimide 
• 74-88-4 methyl iodide 

Downstream Products

• 21419-24-9 3-Amino-2-butanone hydrochloride 
• 70386-38-8 D,L-1-bromo-3-phthalimido-2-butanone 
• 1240790-62-8 C₂₁H₁₆N₄O₂S 
• 1240790-64-0 C₂₀H₁₅N₅O₂S 
• 1240790-66-2 C₁₉H₁₅N₃O₂S 
• 1240790-69-5 C₂₀H₁₇N₃O₂S 
• 1240790-70-8 C₂₅H₁₉N₃O₂S 
• 1240790-71-9 C₂₀H₁₆N₄O₂S 

Relevant academic research and scientific papers

Sulfur ylides 9. Resonance electron capture by molecules of keto-stabilized sulfur ylides containing a phthalimide fragment

The mass spectra of negative ions of keto-stabilized sulfur and phosphorus ylides (obtained from amino acids) and products of their thermal conversion are studied. The most characteristic peaks in the mass spectra of ylides belong to negative molecular ions and to [M - H]- ions. Peaks of fragment ions in the mass spectra of ylides and products of their thermal conversion coincide both in mass numbers and resonance energies.

Preparation method of ftibamzone

The invention discloses a preparation method of ftibamzone. The preparation method comprises the following steps: firstly, preparing 3-phthalimide butanone from phthalimide potassium salt and 3-chlorobutanone; reacting the 3-phthalimide butanone with dry hydrogen bromide gas in a dimethyl sulfoxide solution to prepare a dimethyl sulfoxide solution of 3-phthalimide-2-oxy-n-butyraldehyde; dropwise adding a thiosemicarbazide solution into the dimethyl sulfoxide solution of the 3-phthalimide-2-oxy-n-butyraldehyde, controlling the reaction temperature, carrying out heat preservation reaction to prepare a crude product, and recrystallizing the crude product to obtain the ftibamzone. The technical scheme has the advantages of few reaction steps, high yield and high purity.

Preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide

The invention relates to a preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide (I). The preparation method comprises the steps: adopting alanine and N-ethoxycarbonyl phthalimide as a starting material, and performing aminoacylation, methyl-lithium addition, an oxidation reaction and a condensation reaction so as to obtain the target product 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide (I). The method for synthesizing 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide has the advantages of few reaction steps, simple operation, suitability for large-scale production and the like.

Method for synthesizing 3 - phthalatic imide - 2 - oxo-butyl - 1, 2 - double-thiosemicarbazone method

The invention relates to a novel method of synthesizing 3-phthalimide-2-oxobutryaldehyde-1, 2-bis-thiosemicarbazide. The novel method comprises the following steps: synthesizing 3-nitro-2-butanol with acetaldehyde and nitroethane as starting raw materials, then carrying out reduction on 3-nitro-2-butanol to generate 3-amino-2-butanol, carrying out reaction on 3-amino-2-butanol and phthalic anhydride to generate N-(1-methyl-2-hydroxypropyl) phthalimide, respectively carrying out oxidation by two steps to form 3-phthalimide-2-oxo-butyraldehyde, and finally carrying out condensation on 3-phthalimide-2-oxo-butyraldehyde and thiosemicarbazide to obtain a target product. The 3-phthalimide-2-oxobutryaldehyde-1, 2-bis-thiosemicarbazide has obvious inhibition action on replication of herpes simplex I type (HSV-I) and II I type (HSV-II) viruses in tissue culture cells; at present, the 3-phthalimide-2-oxobutryaldehyde-1, 2-bis-thiosemicarbazide is mainly clinically used for treating skin diseases caused by herpesvirus and sexually transmitted diseases caused by human papillomavirus (HSV) and has good curative effect.

Efficient preparation of biologically important 1,2-amino alcohols

An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH 3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60C to yield biologically important 1,2-amino alcohols.

Aldehyde-selective wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst

Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt. Copyright

Synthesis and antiviral activity of phthiobuzone analogues

A series of phthiobuzone analogs, prepared from potassium phthalimide or phthalandione, have been evaluated for their antiviral activities. Among the candidates, compounds 5j and 5k, which contain the substituted 4-halogenated phenyl ring at N-4′,4″ position, show more potent antiviral activity than phthiobuzone against herpes simplex virus 1 (IC50=8.56 and 2.85 μ/ml, respectively) and herpes simplex virus 2 (IC50=1.75 and 4.11μg/ ml, respectively). Compounds 9c and 9d with a propylene linker between the phthalimide and bisthiosemicarbazone moieties display similar antiviral potency against herpes simplex virus 1 (IC50=2.85 and 4.11 μg/ml, respectively).

Synthesis and cytotoxic activity of heterocycle-substituted phthalimide derivatives

A series of heterocycle-substituted phthalimide derivatives were synthesized. Structurally diverse derivatives with heterocyclic rings, including furan, imidazo[1,2-a]pyridine, 1,3,4-thiadiazine, imidazo[2,1-b][1,3,4] thiadiazine, pyrazole, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine, thiazole and thiazoline, were obtained by the reactions of α-bromoketone intermediate with various nucleophiles containing oxygen, nitrogen and sulfur atom. Their cytotoxic activity was also evaluated against five human cancer cell lines in vitro.

Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines

Convenient syntheses of 1H-pyrazin-2-ones and 2-aminopyrazines are described. By coupling Boc-protected amino acids with α-amino ketones or with amino alcohols and subsequent oxidation, 1H-pyrazin-2-ones were obtained. Transformation into the corresponding pyrazine triflates and substitution with primary or secondary amines led to 2-aminopyrazines. Since these syntheses take advantage of the use of readily available starting materials (e.g., amino acids, aminoalcohols and amines) a variety of the entitled structures can be obtained in few, high yielding steps.

AMIDOACETONE ENOLATE ANIONS: ALKYLATION AND MICHAEL REACTION

The lithyum enolate derived from benzamidoacetone (1) can be regiospecifically alkylated at C(1) and stereospecifically added in conjugate fashion to cyclohexenone without resorting to protection of free NH.Comparison is made with alkylations of methyl hippurate.