124401-38-3

Basic information

• Product Name: N-Phenyl-isobutyloylacetamide
• Synonyms: N-PHENYL-ISOBUTYLOYLACETAMIDE;N-PHENYL ISOBUTYRYLACETAMIDE;4-Methyl-3-oxopentanoic acid anilide;4-methyl-3-oxo-n-phenyl-pentanamide;4-methyl-3-oxopentanoic acid phenylamide;4-METHYL-3-OXO-PENTANOIC PHENYLAMIDE;Isobutyrylacetanilide;N-PhNeyl-isobutyloyl Acetamide
• CAS NO: 124401-38-3
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• EINECS: 1308068-626-2
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatics Compounds;Aromatics;Miscellaneous Reagents;Atorvastatin intermediates;INTERMEDIATES OF ATORVASTATIN
• Mol File: 124401-38-3.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 384.409 °C at 760 mmHg
• Flash Point: 159°C
• Appearance: Yellow oil
• Density: 1.103
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Metahnol (Slightly)
• PKA: 12.14±0.46(Predicted)
• CAS DataBase Reference: N-Phenyl-isobutyloylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenyl-isobutyloylacetamide(124401-38-3)
• EPA Substance Registry System: N-Phenyl-isobutyloylacetamide(124401-38-3)

Safety Data

• Hazardous Substances Data: 124401-38-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

N-Phenyl Isobutyrylacetamide (cas# 124401-38-3) is a compound useful in organic synthesis.

InChI:InChI=1/C12H15NO2/c1-9(2)11(14)8-12(15)13-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3,(H,13,15)

Synthetic route

Methyl 4-methyl-3-oxopentanoate (42558-54-3) + aniline (62-53-3) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With dmap at 100℃; for 16h;	96.4%
With triethylamine at 80 - 125℃;	92.7%
With sodium hydroxide In neat (no solvent) at 135℃; for 12h;	92%

aniline (62-53-3) + isobutyryl Meldrum's acid → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
In toluene Acylation; ring cleavage; Heating;	96%

aniline (62-53-3) + ethyl 4-methyl-3-oxo-pentanoate (7152-15-0) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With triethylamine In toluene for 4h; Reflux;	92%
In toluene for 3h; Reflux;	81%
With acetic acid In toluene for 4h; Heating;	66%
With pyridine In toluene for 16h; Reflux;

C21H31N3O4 (1236069-48-9) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.666667h;	88%

ethyl 4-methyl-3-oxo-pentanoate (7152-15-0) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With aniline In acetic acid; ethyl acetate; toluene	66%

Methyl 4-methyl-3-oxopentanoate (42558-54-3) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With ethylenediamine; aniline In water; toluene
With aniline In water; ethylenediamine; toluene

toluene-water + Methyl 4-methyl-3-oxopentanoate (42558-54-3) → 4-Methyl-3-oxo N phenylpentamide + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With ethylenediamine; aniline In water; toluene

toluene-water + Methyl 4-methyl-3-oxopentanoate (42558-54-3) → 4-Methyl-3-oxo-N-phenylpentamide + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With ethylenediamine; aniline In water; toluene

3-methyl-butan-2-one (563-80-4) + phenyl isocyanate (103-71-9) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With sodium hydride In toluene; mineral oil Inert atmosphere; Reflux;

3-methyl-butan-2-one (563-80-4) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.17 h / 20 °C 1.2: 3 h / 50 °C 2.1: triethylamine / toluene / 6 h / 70 - 120 °C View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere 2: ethylenediamine / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 140 - 150 °C / Inert atmosphere View Scheme

isobutyrylacetic acid (5650-76-0) + aniline (62-53-3) → 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3)

Conditions	Yield
With triethylamine In toluene at 85℃; for 4h;	67 g

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 2,2-Difluoro-4-methyl-3-oxo-N-phenylpentanamide (1439365-82-8)

Conditions	Yield
With Selectfluor In water; acetonitrile at 20℃; for 16h; Schlenk technique; Sealed tube; chemoselective reaction;	99%
With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2 2 2]octane bis(tetrafluoroborate); potassium carbonate In water at 20℃; for 15h;	94%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 2-fluoro-4-methyl-3-oxo-N-phenylpentanamide (1026394-65-9)

Conditions	Yield
With Selectfluor In PEG-400 at 60℃; for 17h;	96%
With Selectfluor In water; acetonitrile at 20℃; for 4h; Schlenk technique; Sealed tube; chemoselective reaction;	94%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → C12H16N2O

Conditions	Yield
With ammonium carbamate In methanol at 20℃;	96%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + benzaldehyde (100-52-7) → 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide (125971-57-5)

Conditions	Yield
With 4-amino-phenol; acetic acid In hexane for 24h; Reflux;	94%
With acetic acid; 3-amino propanoic acid In hexane Heating;	85%
With ionic tagged amine supported on magneticnanoparticle In water at 80℃; for 4h; Knoevenagel Condensation;	84%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + benzohydroximoyl chloride (698-16-8) → 5-isopropyl-N,3-diphenylisoxazole-4-carboxamide

Conditions	Yield
With triethylamine; N,N,N',N'-tetramethylguanidine In methanol at 80℃; for 48h; Inert atmosphere;	93%
With triethylamine; N,N,N',N'-tetramethylguanidine In methanol at 80℃; for 48h; regioselective reaction;	72%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 2-bromo-4-methyl-3-oxo-pentanoic acid phenylamide (807361-46-2)

Conditions	Yield
With N-Bromosuccinimide In acetone for 3h;	92%
With bromine In chloroform for 0.5h;	80%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + N-phenylbenzohydrazonoyl chloride (15424-14-3) → 5-isopropyl-N,1,3-triphenyl-1H-pyrazole-4-carboxamide

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 72h; Inert atmosphere; Green chemistry;	92%
With dmap; triethylamine In chloroform at 80℃; for 48h; regioselective reaction;	92%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + benzaldehyde (100-52-7) → 4-Methyl-3-oxo-N-phenyl-2(phenylmethylene)pentanamide (222320-29-8)

Conditions	Yield
With acetic acid; 3-amino propanoic acid In hexane Heating;	90%
With acetic acid In toluene

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + 2-diazo-5-methylcyclohexane-1,3-dione (158836-48-7) → (E)-3-(1-hydroxy-2-methylpropylidene)-6-methyl-3,5,6,7-tetrahydrobenzofuran-2,4-dione

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; acetic acid In 1,2-dichloro-ethane at 70℃; for 4h; Inert atmosphere; chemoselective reaction;	90%

diazodimedone (1807-68-7) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → (E)-3-(1-hydroxy-2-methylpropylidene)-6,6-dimethyl-3,5,6,7-tetrahydrobenzofuran-2,4-dione

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; acetic acid In 1,2-dichloro-ethane at 70℃; for 4h; Inert atmosphere; chemoselective reaction;	89%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + benzaldehyde (100-52-7) → 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene) pentanamide (222320-17-4)

Conditions	Yield
With amine functionalized silica coated Fe3O4 nanoparticles In water at 20℃; for 0.416667h; Knoevenagel Condensation; Sonication; Green chemistry;	87%
With acetic acid; 3-amino propanoic acid In toluene at 130℃; for 12h;	29.18%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + 2,6-di-tert-butyl-4-(2-hydroxybenzylidene)-2,5-cyclohexadiene-1-one → C33H43NO4

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 48h; Inert atmosphere;	87%

3-Phenyl-2-propyn-1-ol (1504-58-1) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 3-iso-butyryl-1,4-diphenyl-2-pyridone (1416150-78-1)

Conditions	Yield
With 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine; ruthenium(IV) oxide hydrate; oxygen In tetrahydrofuran under 760.051 Torr; for 12h; Reflux; regioselective reaction;	86%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + 2-diazo-5-furan-2-yl-cyclohexane-1,3-dione → (E)-6-(furan-2-yl)-3-(1-hydroxy-2-methylpropylidene)-3,5,6,7-tetrahydrobenzofuran-2,4-dione

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; acetic acid In 1,2-dichloro-ethane at 70℃; for 4h; Inert atmosphere; chemoselective reaction;	86%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + cyclohexylamine (108-91-8) → 3-(cyclohexylamino)-4-methylpent-2(E)-enoic acid anilide (124401-40-7)

Conditions	Yield
With acetic acid In toluene for 20h; Heating;	82%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + 1-(4-fluoro-phenyl)-2-hydroxy-2-phenylethanone (88522-72-9) → 5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide

Conditions	Yield
With ammonium acetate In acetic acid at 110 - 120℃; for 2h;	81%

2-bromo-1-(4-fluorophenyl)-2-phenylethan-1-one (88675-31-4) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 1-(4-fluorophenyl)-2-phenylethanone (347-84-2) + 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide (125971-96-2)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 5h; Reagent/catalyst; Time; Darkness;	A n/a B 80%

2-bromo-1-(4-fluorophenyl)-2-phenylethan-1-one (88675-31-4) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide (125971-96-2)

Conditions	Yield
With potassium carbonate In acetone for 2h; Reflux;	78%
With potassium carbonate In acetone at 18.5 - 26℃; Product distribution / selectivity;	77.7%
With potassium carbonate In acetone at 18 - 26℃;	74%

(2-nitroethenyl)benzene (102-96-5) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + aniline (62-53-3) → 2-isopropyl-N,1,4-triphenyl-1H-pyrrole-3-carboxamide

Conditions	Yield
With zirconocene dichloride In ethanol at 80℃; for 1.5h;	75%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + propargyl alcohol (107-19-7) → 2-isopropyl-4-methyl-N-phenylfuran-3-carboxamide

Conditions	Yield
With triethylamine; silver carbonate In acetonitrile at 80℃; for 12h; Inert atmosphere; Molecular sieve; regioselective reaction;	75%

2-chloro-1-(4-fluorophenyl)-2-phenylethan-1-one (62148-67-8) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide (125971-96-2)

Conditions	Yield
With potassium carbonate In acetone at 25 - 60℃; Reflux;	74%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + benzalacetophenone (94-41-7) → 2-isopropyl-N,4,6-triphenylnicotinamide (1398101-64-8)

Conditions	Yield
With ammonium cerium (IV) nitrate; ammonium acetate In ethanol at 50℃; for 24h;	74%

4-fluoro-β-nitrostyrene (5153-69-5, 706-08-1) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + aniline (62-53-3) → 4-(4-fluorophenyl)-2-isopropyl-N,1-diphenyl-1H-pyrrole-3-carboxamide (122223-62-5)

Conditions	Yield
With zirconocene dichloride In ethanol at 80℃; for 1.5h;	74%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + 2,6-di-tert-butyl-4-(2-hydroxybenzylidene)-2,5-cyclohexadiene-1-one → C33H39NO3

Conditions

Yield

Stage #1: 4-methyl-3-oxo-N-phenylpentanamide; 2,6-di-tert-butyl-4-(2-hydroxybenzylidene)cyclohex-2,5-diene-1-one With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In dichloromethane at 20℃; for 72h; Stage #2: With toluene-4-sulfonic acid In toluene at 110℃; for 1h; enantioselective reaction;

74%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide (125971-96-2)

Conditions	Yield
With potassium carbonate In isopropyl alcohol at 10 - 45℃; Product distribution / selectivity;	73%
Multi-step reaction with 2 steps 1: β-alanine; glacial acetic acid / hexane / Heating 2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; 4-amino-phenol / hexane / 24 h / Reflux 2.1: triethylamine; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / neat (no solvent) / 16 h / 75 °C / Inert atmosphere 2.2: 4 h / 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: glycine; acetic acid / n-heptane / 8 h / Inert atmosphere; Reflux 2: 10 h / 20 °C / Inert atmosphere View Scheme

4-methyl-β-nitrostyrene (7559-36-6) + 4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + aniline (62-53-3) → 2-isopropyl-N,1-diphenyl-4-p-tolyl-1H-pyrrole-3-carboxamide

Conditions	Yield
With zirconocene dichloride In ethanol at 80℃; for 1.5h;	73%

Upstream product

• 42558-54-3 Methyl 4-methyl-3-oxopentanoate 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 1236069-48-9 C₂₁H₃₁N₃O₄ 
• 563-80-4 3-methyl-butan-2-one 
• 5650-76-0 isobutyrylacetic acid 
• 62-53-3 aniline 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 124401-40-7 3-(cyclohexylamino)-4-methylpent-2(E)-enoic acid anilide 
• 125971-57-5 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide 
• 124401-39-4 3-(isopropylamino)-4-methylpent-2(E)-enoic acid anilide 
• 222412-73-9 (Z)-4-methyl-3-oxo-N-phenyl-2-([2H₅]phenylmethylene)pentamide 
• 222412-74-0 C₁₂⁽¹³⁾C₇H₁₉NO₂ 
• 222320-29-8 4-Methyl-3-oxo-N-phenyl-2(phenylmethylene)pentanamide 
• 1239420-81-5 C₂₁H₂₂N₄O₄ 
• 1239420-83-7 C₂₁H₂₂N₄O₄ 
• 1239420-86-0 C₂₇H₂₇N₃O₃ 
• 1239420-88-2 3-isopropyl-5-phenyl-4-[N-phenylaminocarbonyl]-4,5-dihydro-1H-pyrazole 
• 1239420-90-6 3-isopropyl-5-(p-chlorophenyl)-4-[N-phenylaminocarbonyl]-4,5-dihydro-1H-pyrazole 
• 1239420-92-8 3-isopropyl-5-(o-chlorophenyl)-4-[N-phenylaminocarbonyl]-4,5-dihydro-1H-pyrazole 
• 1239420-94-0 3-isopropyl-5-(p-fluorophenyl)-4-[N-phenylaminocarbonyl]-4,5-dihydro-1H-pyrazole 
• 1239420-96-2 C₁₉H₂₁N₃O₂ 

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