2835-77-0

Basic information

• Product Name: 2-Aminobenzophenone
• Synonyms: O-AMINOBENZOPHENONE;O-BENZOYLANILINE;TIMTEC-BB SBB003573;2-AMINOPHENYL PHENYL KETONE;(2-AMINOPHENYL)(PHENYL)METHANONE;2-BENZOYLANILINE;2-AMINOBENZOPHENONE;ABP
• CAS NO: 2835-77-0
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23
• EINECS: 220-613-9
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Benzophenones & Derivatives (substituted);API
• Mol File: 2835-77-0.mol
• Article Data: 110

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 280°C
• Flash Point: 240 °C
• Appearance: Yellow-gold/Fine Crystalline Powder
• Density: 1.0957 (rough estimate)
• Vapor Pressure: 4.31E-06mmHg at 25°C
• Refractive Index: 1.6050 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO, Methanol
• PKA: 0.33±0.10(Predicted)
• Water Solubility: practically insoluble
• BRN: 743425
• CAS DataBase Reference: 2-Aminobenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminobenzophenone(2835-77-0)
• EPA Substance Registry System: 2-Aminobenzophenone(2835-77-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2835-77-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow-gold fine crystalline powder

Uses

Different sources of media describe the Uses of 2835-77-0 differently. You can refer to the following data:
1. 2-Aminobenzophenone is a derivative of Benzophenone (B204980), used in the manufacturing of antihistamines, hypnotics, insecticides. 2-Aminobenzophenone was shown to exhibit modulation activity of GAB AA receptor-mediated currents in isolated purkinje neurons.
2. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuffs.

InChI:InChI=1/C13H11NO/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-9H,14H2

Synthetic route

2-(tosylamino)benzophenone (1859-71-8) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
Stage #1: 2-(tosylamino)benzophenone With sulfuric acid at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With sodium hydrogencarbonate Inert atmosphere; Schlenk technique;	100%
With sulfuric acid at 120℃; for 0.25h;	6.63 g
With sulfuric acid; water at 120℃; for 0.25h;

(2-aminophenyl)(phenyl)methanol (13209-38-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen In acetonitrile at 60℃; for 0.5h;	98%
With copper(II) chloride monohydrate; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;

4-ethoxy-4-phenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-one (111838-36-9) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With sulfuric acid for 0.25h; Ambient temperature;	96.6%

2-nitrobenzophenone (2243-79-0) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With sodium tetrahydroborate In water at 40℃; for 2h; chemoselective reaction;	95%
With iron; acetic acid
With nickel; ethyl acetate Hydrogenation;

2-Aminobenzophenone N,N-dimethylhydrazone → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With potassium carbonate; dimethyl sulfate In acetonitrile Heating;	95%
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.166667h; Hydrolysis;	92%

(2-nitrophenyl)phenylmethanol (5176-12-5) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr; for 5h;	95%
Multi-step reaction with 3 steps 1: 93 percent / MnO2 / CH2Cl2 / 20 h / Heating 2: 73 percent / hydroxylamine hydrochloride / ethanol; pyridine / 30 h / Heating 3: 17 percent / CO; pentamethylcyclopentadienyl dicarbonyl iron(II) dimer / dioxane / 75 h / 150 °C / 38000 Torr View Scheme

3-phenyl-2,1-benzoxazole (5176-14-7) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; triethylamine In tetrahydrofuran at 25℃; under 7500.75 Torr; for 12h; Autoclave;	95%
With samarium diiodide In tetrahydrofuran at 60℃;	60%

(2-azidophenyl)(phenyl)methanone (16714-27-5) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With ammonia; iron(II) sulfate In methanol; water at 20℃; for 2.5h; Reduction;	94%
With methanol; sodium sulfide for 0.166667h;	70%

anthranilic acid nitrile (1885-29-6) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate; water In 2-methyltetrahydrofuran at 80℃; for 36h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique;	93%
With [2,2]bipyridinyl; potassium fluoride; acetic acid; palladium diacetate In tetrahydrofuran at 80℃; for 48h;	31%
With potassium fluoride; 5,5'-dimethyl-2,2'-bipyridine; bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid In N,N-dimethyl-formamide at 80℃; for 48h; Sealed tube; Schlenk technique;	11%
With [2,2]bipyridinyl; methanesulfonic acid; palladium diacetate In tetrahydrofuran
With [2,2]bipyridinyl; methanesulfonic acid; palladium(II) trifluoroacetate In tetrahydrofuran; water at 80℃; for 36h;

carbon monoxide (201230-82-2) + 2-iodophenylamine (615-43-0) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
Stage #1: 2-iodophenylamine; phenylboronic acid With potassium carbonate In toluene for 0.166667h; Suzuki cross-coupling reaction; Autoclave; Stage #2: carbon monoxide In toluene at 100℃; under 5171.62 Torr; for 10h; Suzuki cross-coupling reaction; Autoclave;	93%
With potassium carbonate In methoxybenzene at 80℃; under 760.051 Torr; for 12h; carbonylative Suzuki-Miyaura cross-coupling;	89%
With potassium carbonate under 11251.1 Torr; for 0.5h; Suzuki-Miyaura Coupling; Autoclave; Reflux;	89%

2-phenylethynylaniline (13141-38-3) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With potassium tert-butylate; oxygen; copper diacetate In toluene at 100℃; under 760.051 Torr; for 12h;	92%
Multi-step reaction with 2 steps 1: copper diacetate; potassium tert-butylate; oxygen / dimethyl sulfoxide / 24 h / 120 °C / 760.05 Torr 2: copper diacetate; potassium tert-butylate; oxygen / dimethyl sulfoxide / 24 h / 120 °C / 760.05 Torr View Scheme
Multi-step reaction with 2 steps 1: benzonitrile; copper diacetate; potassium tert-butylate / dimethyl sulfoxide / 24 h / 120 °C / Inert atmosphere 2: copper diacetate; potassium tert-butylate; oxygen / dimethyl sulfoxide / 24 h / 120 °C / 760.05 Torr View Scheme

pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide (124522-52-7) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With ethanol; sodium hydroxide at 70℃; for 3h;	91%

sodium benzenesulfonate (873-55-2) + anthranilic acid nitrile (1885-29-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With [2,2]bipyridinyl; p-nitrobenzenesulfonic acid; palladium diacetate In tetrahydrofuran; water at 80℃; for 48h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	91%

2-iodophenylamine (615-43-0) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With sodium t-butanolate In N,N-dimethyl acetamide at 80℃; for 0.833333h; Suzuki Coupling;	91%

4-methoxy-4-phenyl-1,2-dihydro-3,1-benzoxazine-2(4H)-one (91148-63-9) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With sulfuric acid for 0.25h; Ambient temperature;	88.2%

anthranilic acid (118-92-3) + benzene (71-43-2) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With trifluorormethanesulfonic acid; tris(methyl salicylate)phoshate ester at 20℃; for 0.333333h; Reagent/catalyst; chemoselective reaction;	88%
With trifluorormethanesulfonic acid; tris(methyl salicylate)phoshate ester at 20℃; for 0.333333h;	88%
With PPA In dichloromethane at 80℃; for 2h; Friedel-Crafts acylation;	48%

anthranilic acid nitrile (1885-29-6) + benzene (71-43-2) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
Stage #1: anthranilic acid nitrile; benzene With trifluorormethanesulfonic acid In dichloromethane at 60 - 80℃; Houben-Housch synthesis; Inert atmosphere; Stage #2: With water In dichloromethane Houben-Housch synthesis; Inert atmosphere; Cooling with ice; Stage #3: With sodium hydroxide In water Inert atmosphere;	88%

chloroform (67-66-3) + 2-iodophenylamine (615-43-0) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With potassium hydroxide In toluene at 60℃; for 8h; Suzuki-Miyaura Coupling; Sealed tube; Green chemistry;	87%

2-acetamidobenzophenone (85-99-4) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With hydrogenchloride In water at 125℃; for 3h;	86%
With hydrogenchloride
With hydrogenchloride In methanol; water at 60℃; for 3h; Schlenk technique; Inert atmosphere;	56.7 mg

2-acetamidobenzophenone (85-99-4) → 4-phenyl-2-quinolinone (5855-57-2) + (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 2.5h; Heating;	A 83% B 16%
With sodium methylate In N,N-dimethyl-formamide at 100℃; for 3h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;
With potassium carbonate In tetrahydrofuran at 80℃; for 3h; Schlenk technique; Inert atmosphere;

2-iodophenylamine (615-43-0) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With carbon monoxide; potassium carbonate In toluene at 120℃; under 22502.3 Torr; for 12h; Suzuki Coupling; Autoclave;	83%

N-phenyl benzoyl amide (93-98-1) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With zirconium(IV) oxychloride at 160 - 180℃; for 0.5h;	82%

2-iodophenylamine (615-43-0) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
Stage #1: 9-methyl-9H-fluorene-9-carbonyl chloride With N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate at 80℃; Stage #2: 2-iodophenylamine; phenylboronic acid With potassium carbonate; palladium dichloride at 80℃;	82%

N-phenyl benzoyl amide (93-98-1) → (4-aminophenyl)(phenyl)methanone (1137-41-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
In water Irradiation; sodium dodecyl sulfate micelles;	A 15% B 80%
In methanol at 20 - 25℃; for 48h; Irradiation; Yield given;

isatic acid (484-38-8) + phenylboronic acid (98-80-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With silver carbonate In acetonitrile at 60℃; for 1h;	80%

2-isocyanatobenzoyl chloride (5100-23-2) + benzene (71-43-2) → 4,4-diphenyl-1,4-dihydro-3,1-benzoxazin-2(1H)-one (71526-47-1) + 3-(2'-benzoylphenyl)-1,2,3,4-tetrahydroquinazoline-2,4-dione (91148-55-9) + 3-(2'-benzoylphenyl)-4-(2'-benzoylphenylimino)-1,2,3,4-tetrahydroquinazoline-2-one (91148-57-1) + (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With aluminium trichloride at 18 - 20℃; for 0.75h; Further byproducts given;	A 5% B 3% C 6% D 79%

1-(2-Aminophenyl)-1-phenyl-methanonoxim (51674-05-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With cellulose supported Cu-nanoparticles In water at 100℃; for 0.133333h; Microwave irradiation; Green chemistry;	79%

3-(tert-butylperoxy)-3-phenylindolin-2-one → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 23℃; for 12h; Inert atmosphere;	78%

o-benzoylbenzamide (7500-78-9) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
With sodium hypochlorite; sodium hydroxide In water at 85 - 90℃; Hofmann Rearrangement;	77.1%
With alkaline aqueous sodium hypochlorite solution
With ammonia; potassium amide; potassium nitrate
With sodium hydroxide; sodium hypobromide man versetzt die filtrierte Loesung mit Alkohol;

phenylmagnesium bromide (100-58-3) + anthranilic acid nitrile (1885-29-6) → (2-aminophenyl)(phenyl)methanone (2835-77-0)

Conditions	Yield
Stage #1: phenylmagnesium bromide; anthranilic acid nitrile In tetrahydrofuran at 0 - 20℃; for 13h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; for 12h; Inert atmosphere;	75%
Stage #1: phenylmagnesium bromide; anthranilic acid nitrile In diethyl ether at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether at 0 - 20℃; Inert atmosphere;	23.8%
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 h / 15 °C / Inert atmosphere 2: hydrogenchloride; water / 0.5 h / 60 °C / Inert atmosphere View Scheme
In tetrahydrofuran at 0 - 20℃; for 1.08333h; Inert atmosphere;
In tetrahydrofuran at 0 - 20℃;

acetic anhydride (108-24-7) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2-acetamidobenzophenone (85-99-4)

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	100%
With pyridine	99%
With N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide) at 80℃; for 0.166667h; neat (no solvent);	92%

acetylacetone (123-54-6) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 3-acetyl-2-methyl-4-phenylquinoline (13337-57-0)

Conditions	Yield
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	100%
With sulfuric acid; silica gel at 100℃; for 0.75h; Friedlaender synthesis;	99%
With trifluoroacetic acid at 100℃; for 0.116667h;	99%

(2-aminophenyl)(phenyl)methanone (2835-77-0) → (2-aminophenyl)(phenyl)methanol (13209-38-6)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 2h; Heating;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Reduction;	97%
With sodium tetrahydroborate In methanol at 0℃;	97%

2-Bromoacetyl bromide (598-21-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2'-benzoyl-2-bromo-acetanilide (14439-71-5)

Conditions	Yield
	100%
With potassium carbonate In acetonitrile at 20℃; for 1h;	98%
With potassium carbonate In acetonitrile at 20℃; for 1h;	98%

acetylenedicarboxylic acid diethyl ester (762-21-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → diethyl 4-phenylquinoline-2,3-dicarboxylate (17282-95-0)

Conditions	Yield
With indium(III) chloride at 80℃; for 3h;	100%
With indium(III) chloride at 80℃; for 0.833333h; regioselective reaction;	94%
Stage #1: acetylenedicarboxylic acid diethyl ester With pyridine at 0 - 10℃; for 0.25h; Stage #2: (2-aminophenyl)(phenyl)methanone at 20℃; for 15h;	88%

1,3-cylohexanedione (504-02-9) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 9-phenyl-3,4-dihydro-2H-acridin-1-one (17401-27-3)

Conditions	Yield
With o-benzenedisulfonimide at 80℃; for 4h; Friedlaender synthesis; Neat (no solvent);	100%
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	100%
With aluminum oxide In chloroform for 3h; Friedlaender reaction; Reflux;	98%

cyclohexanone (108-94-1) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 9-phenyl-1,2,3,4-tetrahydroacridine (10265-83-5)

Conditions	Yield
With o-benzenedisulfonimide at 80℃; for 6h; Friedlaender synthesis; Neat (no solvent);	100%
With citric acid at 100℃; for 4h; Friedlaender synthesis; neat (no solvent);	99%
With ammonium cerium (IV) nitrate In ethanol for 8h; Friedlaender synthesis; Reflux;	98%

dimedone (126-81-8) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 3,3-dimethyl-9-phenyl-3,4-dihydro-2H-acridin-1-one (17282-85-8)

Conditions	Yield
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	100%
scandium tris(dodecyl sulfate) In water at 40℃; Friedlaender annulation;	99%
With aluminum oxide In chloroform for 3h; Friedlaender reaction; Reflux;	98%

phenylacetylene (536-74-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 1-(2-aminophenyl)-1,3-diphenylprop-2-yn-1-ol

Conditions	Yield
With potassium tert-butylate In neat (no solvent) at 20℃; for 2h; Inert atmosphere; Green chemistry;	100%
Stage #1: phenylacetylene With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 2h; Stage #2: (2-aminophenyl)(phenyl)methanone In tetrahydrofuran at 50℃; Further stages.;
Stage #1: phenylacetylene With ethyl bromide; magnesium In tetrahydrofuran at 0 - 50℃; Inert atmosphere; Reflux; Stage #2: (2-aminophenyl)(phenyl)methanone In tetrahydrofuran at 50℃; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran Saturated solution;
With potassium tert-butylate In neat (no solvent) at 20℃; for 2h; Inert atmosphere;
With potassium tert-butylate at 20℃; for 2h; Inert atmosphere;

phenylacetyl chloride (103-80-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → N-(2-benzoylphenyl)-2-phenylacetamide (342603-80-9)

Conditions	Yield
With pyridine In dichloromethane for 3h;	100%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → (S)-tert-butyl 2-{[(2-benzoylphenyl)amino]carbonyl}pyrrolidine-1-carboxylate (1093987-00-8)

Conditions	Yield
With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃;	100%
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: (2-aminophenyl)(phenyl)methanone In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 55℃; for 12h; Reagent/catalyst;	97%
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With 1-methyl-1H-imidazole; methanesulfonyl chloride In dichloromethane at 25℃; for 0.166667h; Stage #2: (2-aminophenyl)(phenyl)methanone In dichloromethane at 50℃; for 36h;	91%
Stage #1: 1-(tert-butoxycarbonyl)-L-proline With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -5 - 25℃; Large scale; Stage #2: (2-aminophenyl)(phenyl)methanone In tetrahydrofuran at 20 - 25℃; Large scale;	75%

2-(benzotriazol-1-yl)-N-(benzyloxycarbonyl)glycine (124676-19-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2- (108895-97-2)

Conditions	Yield
Stage #1: 2-(benzotriazol-1-yl)-N-(benzyloxycarbonyl)glycine With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: (2-aminophenyl)(phenyl)methanone With 4-methyl-morpholine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: With ammonia In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere;	100%

N-Bromosuccinimide (128-08-5) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2-amino-5-bromobenzophenone (39859-36-4)

Conditions	Yield
In dichloromethane at 0 - 20℃;	100%

9H-fluoren-9-ylmethyl N-[(1S)-1-benzyl-2-benzotriazol-1-yl-2-oxoethyl]carbamate (860800-19-7) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → C37H30N2O4

Conditions	Yield
With trifluoroacetic acid In toluene for 3h; Solvent;	100%

(2-aminophenyl)(phenyl)methanone (2835-77-0) → 2-benzylaniline (28059-64-5)

Conditions	Yield
With potassium hydroxide In water at 50℃; for 4h; Reagent/catalyst; Temperature;	99.5%
With sodium In ethanol	90%
With ethoxyethoxyethanol; hydrazine hydrate; potassium hydroxide at 200℃; under 10343.2 Torr; Wolff-Kishner Reduction; Sonication;	82%

diphenyl acetylene (501-65-5) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,3,4-triphenyl quinoline (10380-73-1)

Conditions	Yield
With 18-crown-6 ether; trifluorormethanesulfonic acid; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In toluene; acetonitrile at 105℃; for 11h; Reagent/catalyst; Solvent; Sealed tube;	99.1%
With palladium(II) bromide; Trimethylacetic acid In benzonitrile; 1,2-dichloro-ethane at 130℃; for 18h; Reagent/catalyst; Solvent; Temperature; Sealed tube;	83%

benzoyl chloride (98-88-4) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → N-(2-benzoylphenyl)benzamide (29670-64-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	99%
With pyridine In dichloromethane Ambient temperature;	94%
In dichloromethane at 20℃; for 1h;	85%
With pyridine
With triethylamine In dichloromethane for 4h;

2-(benzotriazol-1-yl)-N-(benzyloxycarbonyl)glycine (124676-19-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → benzyl N-[[(2-benzoylphenyl)carbamoyl](1H-1,2,3-benzotriazol-1-yl)methyl]carbamate (161365-74-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	99%
Stage #1: 2-(benzotriazol-1-yl)-N-(benzyloxycarbonyl)glycine With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h; Stage #2: (2-aminophenyl)(phenyl)methanone With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; for 0.5h;	87%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide at 0 - 25℃;
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0 - 20℃;
Stage #1: 2-(benzotriazol-1-yl)-N-(benzyloxycarbonyl)glycine With oxalyl dichloride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: (2-aminophenyl)(phenyl)methanone With 4-methyl-morpholine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;

phenylacetylene (536-74-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,4-diphenylquinoline (1039-51-6)

Conditions	Yield
With tetrafluoroboric acid; water; dodecacarbonyl-triangulo-triruthenium In toluene at 160℃; for 12h; Addition; Hydroamination;	99%
With potassium dodeca tungstocobaltate trihydrate at 110℃; for 0.25h; Microwave irradiation; neat (no solvent);	95%
With indium(III) chloride In acetonitrile for 3h; Reflux; regioselective reaction;	93%

1,3-diacetylbenzene (6781-42-6) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 1,3-bis(4'-phenyl-2'-quinolinyl)benzene (321882-19-3)

Conditions	Yield
With phosphorus pentaoxide; 3-methyl-phenol at 135℃; Friedlaender reaction;	99%

ethyl acetoacetate (141-97-9) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 3-acetyl-4-phenyl-1,2-dihydroquinolin-2-one (313273-62-0)

Conditions	Yield
With zeolitic imidazolate framework-8 catalyst In toluene at 90℃; for 24h; Friedlaender Quinoline Synthesis;	99%
With SBA-15/AP mesoporous materials at 89.84℃; for 6h; Friedlaender synthesis; neat (no solvent);	96%
With Amberlite Na sr1L at 115℃; for 0.0833333h; Microwave irradiation; Neat (no solvent);	90.2%

cyclopentanone (120-92-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 9-phenyl-2,3-dihydro-1H-cyclopenta[b]quinoline (10265-82-4)

Conditions	Yield
With acetic acid at 160℃; for 0.0833333h; Friedlaender Quinoline Synthesis; Microwave irradiation;	99%
With ammonium cerium (IV) nitrate In ethanol for 6h; Friedlaender synthesis; Reflux;	98%
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	97%

acetoacetic acid methyl ester (105-45-3) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → methyl 2-methyl-4-phenylquinoline-3-carboxylate

Conditions	Yield
scandium tris(dodecyl sulfate) In water at 40℃; Friedlaender annulation;	99%
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	98%
With magnetic Fe-Cr-Ni oxide alloy nano-belts In water at 20℃; for 0.583333h;	98%

(2-aminophenyl)(phenyl)methanone (2835-77-0) → 2-amino-5-bromobenzophenone (39859-36-4)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 3h;	99%
With sodium perborate; ammonium molybdate(VI) tetrahydrate; potassium bromide In acetic acid at 0℃; for 3h;	96%
With sodium perborate; ammonium molibdate; potassium bromide In acetic acid at 0℃; for 3h;	96%

1-Phenylethanol (98-85-1, 13323-81-4) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 2,4-diphenylquinoline (1039-51-6)

Conditions	Yield
With benzophenone; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II); potassium tert-butylate at 100℃; for 48h; indirect Friedlaender annulation;	99%
With potassium hydroxide at 80℃; for 7h; Friedlaender Quinoline Synthesis;	83%

1-(4-trifluorophenyl)ethanol (1737-26-4) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 4-phenyl-2-(4-(trifluoromethyl)phenyl)quinoline

Conditions	Yield
With benzophenone; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II); potassium tert-butylate at 100℃; for 48h; indirect Friedlaender annulation;	99%

Tetrahydro-4H-pyran-4-one (29943-42-8) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 10-phenyl-3,4-dihydro-1H-pyrano[4,3-b]quinoline (17517-75-8)

Conditions	Yield
With acetic acid at 160℃; for 0.0833333h; Friedlaender Quinoline Synthesis; Microwave irradiation;	99%
With magnesium chloride hexahydrate; toluene-4-sulfonic acid In acetonitrile at 50℃; for 0.666667h; Friedlaender synthesis;	94%
With lithium bromide In acetonitrile at 50℃; for 1.5h; Friedlaender heteroannulation;	80%

ethyl acetoacetate (141-97-9) + (2-aminophenyl)(phenyl)methanone (2835-77-0) + malononitrile (109-77-3) → 6-amino-4-(2-aminophenyl)-2,4-dihydro-3-methyl-4-phenylpyrano[2,3-c]pyrazole-5-carbonitrile (1235990-71-2)

Conditions	Yield
With hydrazine hydrate; heptakis(6-amino-6-deoxy)-β-cyclodextrin at 20℃; for 0.0166667h; Neat (no solvent);	99%

N,N-dimethyl acetamide (127-19-5) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 4-phenylquinazoline (17629-01-5)

Conditions	Yield
With tert.-butylhydroperoxide; N-iodo-succinimide; ammonia In water at 120℃; for 4h;	99%
With ammonium acetate; oxygen; acetic acid; copper(l) chloride at 110℃; under 760.051 Torr; for 12h; Schlenk technique; Green chemistry;	82%

Upstream product

• 7647-01-0 hydrogenchloride 
• 854162-51-9 5-phenyl-benzo[d][1,2,6]oxadiazepine 
• 7139-42-6 6,12-diphenyl-dibenzo<1,5>diazocine 
• 139018-14-7 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one 
• 7732-18-5 water 
• 7722-84-1 dihydrogen peroxide 
• 88092-64-2 2-Acetylamino-3,5-dibromobenzophenone 
• 118-48-9 isatoic anhydride 
• 10282-57-2 2-bromobenzanilide 
• 15310-01-7 benodanil 
• 71-43-2 benzene 
• 5100-23-2 2-isocyanatobenzoyl chloride 
• 118-92-3 anthranilic acid 
• 72349-31-6 (2-(allylamino)phenyl)(phenyl)methanone 

Downstream Products

• 61964-62-3 1-(2-benzoylphenyl)-3-phenylthiourea 
• 111838-37-0 2-{Phenyl-[(E)-phenylimino]-methyl}-phenylamine 
• 21820-08-6 10-phenyl-benzo-1,5-naphthyridine 
• 41296-65-5 Thiophene-2-carboxylic acid (2-benzoyl-phenyl)-amide 
• 124522-52-7 pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide 
• 85422-43-1 9-phenylfuro[3,4-b]quinoline-1(3H)-one 
• 41242-32-4 N-(2-Benzoyl-phenyl)-succinamic acid 
• 113802-25-8 4-Phenyl-3-piperidin-1-ylmethyl-quinolin-2-ylamine 
• 20364-46-9 4-phenyl-2-(2'-pyridinyl)quinoline 
• 71961-29-0 C₂₆H₂₂N₄ 
• 19069-87-5 12-phenyl-isochromeno[3,4-b]quinolin-5-one 
• 22731-27-7 N-(2-Benzoyl-phenyl)-C,C,C-trifluoro-methanesulfonamide 
• 64571-76-2 4-(2-benzoyl-phenyl)-10-phenyl-4H-[1,4]thiazino[3,2-b]quinolin-3-one 
• 50885-16-0 Phenyl-[2-(2,2,2-trifluoro-ethylamino)-phenyl]-methanone 

Relevant articles and documents

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2-(2,1-Benzoxazol-3-yl)-3,5-dimethoxyphenol and 3-phenyl-2,1-benzoxazole

The title compounds, C15H13NO4, (I), and C13H9NO, (II), are produced, along with the corresponding anilines, by the reduction of the appropriate o-nitrobenzophenones. In (I), the planar benzisoxazole and phenol fragments are tilted relative to one another by a rotation of 53.02 (14)° about the bond joining them, and the molecules are linked into chains by phenol O-H...N and phenyl C-H...O oxazole hydrogen bonds. The cell of (II) (space group 12/c) contains eight molecules in general positions, four more in the 2b sites, with twofold axial symmetry that induces a degree of disorder, and a further four as centrosymmetric pairs of complete molecules, each with an occupancy of one-half. The relative tilt of the planar fragments varies slightly from one molecule to another but is much less than that in (I), ranging from 8.8 (8) to 12.58 (15)°.

Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols

A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.

One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.