2958-36-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-2',5-dichlorobenzophenone is used as a key intermediate in the synthesis of lorazepam, a benzodiazepine drug. It is utilized for its anxiolytic properties, helping to alleviate anxiety and related conditions.
Used in Lorazepam Impurity A:
In addition to its role in the production of lorazepam, 2-Amino-2',5-dichlorobenzophenone is also used in the identification and quantification of Lorazepam Impurity A. This is important for ensuring the quality and purity of the final drug product, as well as for regulatory compliance in the pharmaceutical industry.

Synthetic route

5-chloro-3-(2-chlorophenyl)-2,1-benzisoxazole (77792-52-0) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
With iron; acetic acid In ethanol; water at 60 - 70℃; for 2h;	92%

2-amino-5-chlorobenzonitrile (5922-60-1) + 2-Chlorobenzeneboronic acid (3900-89-8) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate; water In 2-methyltetrahydrofuran at 80℃; for 36h; Schlenk technique;	52%

o-chlorobenzoyl chloride (609-65-4) + 4-chloro-aniline (106-47-8) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
(i) ZnCl2, (ii) aq. HCl, (iii) H2SO4; Multistep reaction;
With sulfuric acid; acetic acid; zinc(II) chloride 2) H2O, reflux, 18 h; Yield given. Multistep reaction;
With zinc(II) chloride at 200 - 230℃; for 3h;

N-[4-Chloro-2-(2-chloro-benzoyl)-phenyl]-acetimidic acid ethyl ester → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
With toluene-4-sulfonic acid In xylene

lorazepam (846-49-1) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
With hydrogenchloride for 0.5h; Heating; acid hydrolysis;
With hydroxypropyl-α-cyclodextrin In water for 0.75h; Heating;

lormetazepam (848-75-9) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) + lorazepam (846-49-1)

Conditions	Yield
With hydrogenchloride multistep reaction: biotransformation, acid hydrolysis;

lormetazepam (848-75-9) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) + 2',5-dichloro-2-methylaminobenzophenone (5621-86-3)

Conditions	Yield
With hydrogenchloride multistep reaction: acid hydrolysis, photolysis;

ortho-chlorobenzoic acid (118-91-2) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: SOCl2 / Heating 2.1: ZnCl2 / 2 h / 205 °C 2.2: 7- percent H2SO4 / 8 h / Heating View Scheme

2-Chlorophenylacetonitrile (2856-63-5) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 percent / KOH, K2CO3, H2O / benzene; methanol / 2 h / Ambient temperature 2: 92 percent / Fe/AcOH / H2O; ethanol / 2 h / 60 - 70 °C View Scheme

4-chlorobenzonitrile (100-00-5) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 percent / KOH, K2CO3, H2O / benzene; methanol / 2 h / Ambient temperature 2: 92 percent / Fe/AcOH / H2O; ethanol / 2 h / 60 - 70 °C View Scheme

tert-butyl [4-chloro-2-(2-chlorobenzoyl)phenyl]carbamate → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
With hydrogenchloride In ethanol; water Reflux;
Stage #1: tert-butyl [4-chloro-2-(2-chlorobenzoyl)phenyl]carbamate With hydrogenchloride; water In ethanol Reflux; Stage #2: With sodium hydrogencarbonate In ethanol; water pH=8;

N-(t-butoxycarbonyl)-4-chloroaniline (18437-66-6) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1.25 h / -40 °C / Inert atmosphere 2.1: hydrogenchloride; water / ethanol / Reflux 2.2: pH 8 View Scheme

4-chloro-aniline (106-47-8) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / toluene / 20 °C 2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 1.25 h / -40 °C / Inert atmosphere 3.1: hydrogenchloride; water / ethanol / Reflux 3.2: pH 8 View Scheme

N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (150879-48-4) + 2-bromo-1-chlorobenzene (694-80-4) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;

5-Chloroisatoic anhydride (4743-17-3) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / ethanol / 0.17 h / 20 °C 1.2: 1.5 h / Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine / ethanol; water / 0.17 h / 25 °C 1.2: 1.5 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere View Scheme

5-chloroanthranilic acid (635-21-2) → (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere View Scheme

chloroacetyl chloride (79-04-9) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 2-chloroacetamido-2’,5-dichlorobenzophenone (14405-03-9)

Conditions	Yield
In toluene at 10 - 20℃; for 3.5h;	98.1%
With potassium carbonate In ethyl acetate at 10 - 20℃; for 1h; Cooling with ice;	96.21%
In toluene for 0.0416667h; Microwave irradiation;	88%
With N-ethyl-N,N-diisopropylamine In toluene at 10 - 20℃; for 3.5h;

dimethyl sulfate (77-78-1) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 2',5-dichloro-2-methylaminobenzophenone (5621-86-3)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran at 60℃; for 1h;	98%
With tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran at 20℃; for 1h;

phenylacetylene (536-74-3) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 2-phenyl-4-(2'-chlorophenyl)-6-chloroquinoline

Conditions	Yield
With propylphosphonium tetrachloroindate ionic liquid supported on nanosilica In neat (no solvent) at 110℃; for 0.583333h;	98%
With indium(III) triflate at 110℃; for 0.075h; microwave irradiation;	96%
With potassium dodeca tungstocobaltate trihydrate at 110℃; for 0.166667h; Microwave irradiation; neat (no solvent);	96%

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → (2-azido-5-chlorophenyl)(2-chlorophenyl)methanone

Conditions	Yield
Stage #1: (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone With acetic acid; sodium nitrite In water at 0℃; for 1h; Stage #2: With sodium azide In water for 1h;	98%
Stage #1: (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone With acetic acid; sodium nitrite In water at 0℃; for 1h; Inert atmosphere; Stage #2: With sodium azide In water at 0 - 20℃; Inert atmosphere;	79%
Stage #1: (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 20℃; for 4h;	46%

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) + acetylacetone (123-54-6) → 1-[6-chloro-4-(2-chlorophenyl)-2-methylquinolin-3-yl]ethan-1-one

Conditions	Yield
With 1,3-dimethylimidazolium sulfate monomethyl ester; L-proline at 90℃; for 0.583333h; Knoevenagel Condensation; Green chemistry;	96%
With Nd(NO3)3*6H2O In ethanol at 20℃; Friedlander reaction;	94%
With phosphoric acid In ethanol for 12h; Reflux;	93%

cyclohexane-1,2-dione (765-87-7) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 7-chloro-9-(2'-chlorophenyl)-2,3-dihydroacridin-4(1H)-one

Conditions	Yield
With indium(III) chloride; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 2h;	96%
With sulfuric acid; silica gel In methanol for 2h; Friedlaender Quinoline Synthesis; Reflux;	93%
With eaton’s reagent In neat (no solvent) at 90℃; for 3h;	86%

dimethylglyoxal (431-03-8) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 2-acetyl-6-chloro-4-(2'-chlorophenyl)-quinoline

Conditions	Yield
With indium(III) triflate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 2h; Reagent/catalyst; Temperature; Solvent; Friedlaender Quinoline Synthesis; Ionic liquid;	96%

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 2-amino-5-chloro-α-(2'-chlorophenyl)benzyl alcohol (74067-45-1)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 1.5h; Heating;	95%
With sodium tetrahydroborate In methanol for 2h; Heating / reflux;	91%
With sodium tetrahydroborate In ethanol

methyl 3-cyclopropyl-3-oxopropanoate (32249-35-7) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2-chloro-phenyl)-2-cyclopropyl-quinoline-3-carboxylic acid methyl ester

Conditions	Yield
With aminosulfonic acid at 70℃; for 1h; Product distribution; Further Variations:; Solvents; Temperatures; time; Friedlander condensation;	95%
With aminosulfonic acid at 70℃; for 1h; Friedlander condensation;	95%

N-phthaloylglycine chloride (6780-38-7) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 5,2'-dichloro-2-(phtalimidoacetamido)benzophenone

Conditions	Yield
In chloroform for 6h; Heating;	94%

2-Bromoacetyl bromide (598-21-0) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 2-(2-bromo-acetylamino)-5,2'-dichloro-benzophenone (5504-92-7)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0℃; for 1h;	94%
In diethyl ether at 10℃; for 2h;
In acetonitrile chemoselective reaction;
With sodium carbonate In dichloromethane; water at 0℃; for 2h;

ethyl acetoacetate (141-97-9) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → ethyl 6-chloro-4-(2-chlorophenyl)-2-methyl-3-quinolinecarboxylate

Conditions	Yield
With nickel(II) oxide In ethanol for 3h; Friedlaender Quinoline Synthesis; Reflux; Green chemistry;	94%
With aminosulfonic acid at 70℃; for 1.25h; Friedlander condensation;	91%
With Nd(NO3)3*6H2O In ethanol at 20℃; Friedlander reaction;	87%

1,3-cylohexanedione (504-02-9) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 7-chloro-9-(2'-chlorophenyl)-3,4-dihydroacridin-1(2H)-one

Conditions	Yield
With nickel(II) oxide In ethanol for 3h; Friedlaender Quinoline Synthesis; Reflux; Green chemistry;	93%
With sulfuric acid; silica gel In methanol for 2h; Friedlaender Quinoline Synthesis; Reflux;	93%
With aminosulfonic acid at 70℃; for 0.75h; Friedlander condensation;	89%

5-(trifluoromethyl)-cyclohexane-1,3-dione (124612-15-3) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 7-chloro-9-(2-chlorophenyl)-3-(trifluoromethyl)-3,4-dihydroacridin-1(2H)-one (1052719-52-4)

Conditions	Yield
With hydrogenchloride In water at 60 - 75℃; for 0.5h;	93%

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) + 4-n-methylphenylacetylene (766-97-2) → 6-chloro-4-(2-chlorophenyl)-2-(p-tolyl)quinoline (1285610-45-8)

Conditions	Yield
With potassium dodeca tungstocobaltate trihydrate at 110℃; for 0.25h; Microwave irradiation; neat (no solvent);	93%

acetone (67-64-1) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2-chlorophenyl)-2-methylquinoline

Conditions	Yield
With Nafion NR50 In ethanol at 200℃; for 1h; Microwave irradiation;	93%

cyclohexanone (108-94-1) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 7-chloro-9-(2-chlorophenyl)-1,2,3,4-tetrahydroacridine

Conditions	Yield
With o-benzenedisulfonimide at 80℃; for 4h; Friedlaender synthesis; Neat (no solvent);	92%
With 1,3,5-trichloro-2,4,6-triazine In ethanol for 0.833333h; Friedlander annulation; Heating;	82%
With metal organic framework of 1,3-bis(carboxymethyl)imidazolium barium-1 complex In neat (no solvent) at 80℃; Microwave irradiation;	81%
With silver dodecatungstophosphate In ethanol for 5.5h; Heating;	80%

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 4-(2-chlorophenyl)-6-chloroquinoline-2,3-dicarboxylate (1220115-68-3)

Conditions	Yield
With indium(III) chloride at 80℃; for 0.833333h; regioselective reaction;	92%
Stage #1: acetylenedicarboxylic acid diethyl ester With pyridine at 0 - 10℃; for 0.25h; Stage #2: (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone at 20℃; for 14h;	86%
With β‐cyclodextrin In water at 65 - 75℃; for 6h;	78%

formaldehyd (50-00-0) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → N-[4-chloro-2-(2-chlorobenzoyl)phenyl]formamide (53960-31-9)

Conditions	Yield
In toluene Reflux;	92%

1-methylcyclohexan-4-one (589-92-4) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → C20H17Cl2N

Conditions	Yield
With 1,3-bis(carboxymethyl)-1H-imidazol-3-ium chloride In neat (no solvent) at 100℃; for 16h;	92%

1-phenyl-2-tosylethanone (31378-03-7) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2-chlorophenyl)-2-phenyl-3-tosylquinoline

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 150℃; for 1h; Microwave irradiation;	92%

(2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) + methyl iodide (74-88-4) → 2',5-dichloro-2-methylaminobenzophenone (5621-86-3)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide Ambient temperature;	91%
With potassium carbonate In N,N-dimethyl-formamide at 30℃; for 5h; Concentration; Solvent; Temperature;

1-phenyl-3-dimethylaminoprop-2-enone (1201-93-0) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 3-((4-chloro-2-(2-chlorobenzoyl)phenyl)amino)-1-phenylprop-2-en-1-one

Conditions	Yield
With toluene-4-sulfonic acid In water at 20℃; for 0.333333h; Sonication; chemoselective reaction;	91%

n-hexan-2-one (591-78-6) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2-chloro-phenyl)-2-methyl-3-propyl-quinoline

Conditions	Yield
With aminosulfonic acid at 70℃; for 1.25h; Friedlander condensation;	90%

2-chloro-benzaldehyde (89-98-5) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → C20H11Cl3N2 (1283752-29-3) + 6-chloro-2-(2-chlorophenyl)-4-(2-chlorophenyl)-1,2-dihydroquinazoline (1283752-22-6)

Conditions	Yield
With urea at 140℃; under 8175.82 Torr; for 0.0666667h; Neat (no solvent); Microwave irradiation; Closed vessel;	A n/a B 90%

3-Trifluoromethylbenzaldehyde (454-89-7) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2-chlorophenyl)-2-(3-(trifluoromethyl)phenyl)quinazoline (1372890-88-4)

Conditions	Yield
With Maltose; N,N'-Dimethylurea; ammonium acetate; ammonium chloride at 90℃; for 4h;	90%

acetoacetic acid methyl ester (105-45-3) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → methyl 6-chloro-4-(2-chlorophenyl)-2-methylquinoline-3-carboxylate (1309781-28-9)

Conditions	Yield
With 1,3-bis(carboxymethyl)-1H-imidazol-3-ium chloride In neat (no solvent) at 100℃; for 16h;	90%

dimethyl acetylenedicarboxylate (762-42-5) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → dimethyl 4-(2-chlorophenyl)-6-chloroquinoline-2,3-dicarboxylate (1220115-67-2)

Conditions	Yield
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 110℃; for 4.5h; Green chemistry; regioselective reaction;	89%
With propylphosphonium tetrachloroindate ionic liquid supported on nanosilica In neat (no solvent) at 110℃; for 0.333333h;	88%
Stage #1: dimethyl acetylenedicarboxylate With pyridine at 0 - 10℃; for 0.25h; Stage #2: (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone at 20℃; for 15h;	85%
With β‐cyclodextrin In water at 65 - 75℃; for 6h;	82%

1-ethynyl-3-methoxybenzene (768-70-7) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2-chlorophenyl)-2-(3-methoxyphenyl)-quinoline (1093059-25-6)

Conditions	Yield
With potassium dodeca tungstocobaltate trihydrate at 110℃; for 0.166667h; Microwave irradiation; neat (no solvent);	89%

Upstream product

• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 150879-48-4 N-methyl-N-methyloxy-2-amino-5-chlorobenzamide 
• 694-80-4 2-bromo-1-chlorobenzene 
• 4743-17-3 5-Chloroisatoic anhydride 
• 100-00-5 4-chlorobenzonitrile 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 118-91-2 ortho-chlorobenzoic acid 
• 848-75-9 lormetazepam 
• 846-49-1 lorazepam 
• 77792-52-0 5-chloro-3-(2-chlorophenyl)-2,1-benzisoxazole 
• 609-65-4 o-chlorobenzoyl chloride 
• 106-47-8 4-chloro-aniline 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 

Downstream Products

• 18434-39-4 2'-(o-Chlor-benzoyl)-3.4'-dichlor-propion-anilid 
• 50885-15-9 (2-Chloro-phenyl)-[5-chloro-2-(2,2,2-trifluoro-ethylamino)-phenyl]-methanone 
• 29176-39-4 4-chloro-2-(o-chlorobenzoyl)-N^α-(benzyloxycarbonyl)glycinanilide 
• 23441-87-4 6-chloro-4-(2-chloro-phenyl)-1H-quinazolin-2-one 
• 83520-06-3 2-(N,N-dimethylacetamidino)-2',5-dichlorobenzophenone 
• 85815-52-7 N,N-dimethyl 2-chloro-2-(2-(2-chlorobenzoyl)-5-chlorophenylazo)acetoacetamide 
• 74088-30-5 [({[4-Chloro-2-(2-chloro-benzoyl)-phenylcarbamoyl]-methyl}-carbamoyl)-methyl]-carbamic acid benzyl ester 
• 79039-70-6 2-(4-bromophenyl)-6-chloro-4-(2-chlorophenyl)-quinoline 
• 74088-31-6 N-{[4-Chloro-2-(2-chloro-benzoyl)-phenylcarbamoyl]-methyl}-2-(trityl-amino)-acetamide 
• 76337-81-0 {(S)-1-[4-Chloro-2-(2-chloro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 136623-23-9 C₁₄H₁₃Cl₂N₅*2ClH 
• 136623-23-9 (E)-2-Amino-2',5-dichlorbenzophenonamidinohydrazon dihydrochlorid 
• 136623-23-9 (Z)-2-Amino-2',5-dichlorbenzophenonamidinohydrazon dihydrochlorid 
• 83520-08-5 2-Benzyloxycarbonylamino-N-[4-chloro-2-(2-chloro-benzoyl)-phenyl]-acetimidic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides

The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.

Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution

A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.

Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives

A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.

Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles

An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.

Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles

A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is

Design, synthesis and evaluation of aminobenzophenone derivatives containing nitrogen mustard moiety as potential central nervous system antitumor agent

A series of novel substituted aminobenzophenone derivatives containing nitrogen mustard moiety (5a-f) were synthesized and characterized on the basis of their IR, 1H NMR, 13C NMR, CHN, and mass spectral data. All the compounds when evaluated for chemical 4-(4-nitrobenzyl) pyridine alkylating activity proved to be active alkylating agents. All the synthesized compounds were subjected to physicochemical parameters determination required for central nervous system (CNS) activity through computational, online software, and QikProp 3.2. The log P values and other in silico ADME physicochemical descriptors analyzed lay between the ranges those are required for good BBB penetration. The in vitro antiproliferative activity against human cancer cell lines viz. A 549 (lung), COLO 205 (colon), U 87 (glioblastoma), and IMR-32 (neuroblastoma) was investigated. Most of the test compounds showed potent antitumor activity, especially compound (5f) which displayed the highest activity against CNS cancer cell line comparable to that of chlorambucil and docetaxel. The preliminary structure-activity relationship (SAR) revealed that 5-chloroaminobenzophenone-mustard series (5a-c) exhibited better antitumor activity than 5-nitroaminobenzophenone-mustard series (5d-f).

Synthesis of 2-aminobenzophenone derivatives and their anticancer activity

A number of 2-aminobenzophenones have been synthesized by acylation of para-chloroaniline with different 2-, 3-, 4-chloro-or fluorobenzoyl chloride in solid state via the Friedel-Crafts reaction. Synthesized compounds were characterized by 1H and 13C NMR, Fourier transform-infrared, ultraviolet-visible spectroscopy, mass spectrometry, and elemental analysis. Evaluation of biological activity in vitro showed that the selected compounds 9, 10, and 13 have potential anticancer activity. The presence of one chlorine atom in the second aromatic ring of the benzophenone molecule makes it more active.

Synthesis of quinolin-2-one alkaloid derivatives and their inhibitory activities against HIV-1 reverse transcriptase

Based on an established common pharmacophore of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNTTIs), a series of quinolin-2-one derivatives were synthesized and assayed for their in vitro activities against HIV-1 reverse transcriptase (RT) for the first time. Some of the tested compounds were active against HIV-1 RT. Compounds 4a2 and 4d2 showed inhibitory activities with IC50 values of 0.21 and 0.15 μM, respectively, with a mode of interaction with RT residues of the allosteric pocket similar to that of efavirenz.

Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives

A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).

Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof

The present invention relates to sulfonyl-containing 2,3-diarylindole, especially to new compounds of general Formula, to a preparation method for their preparation, to pharmaceutical compositions containing said compound, and to the medical use thereof in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).