619-17-0

Basic information

• Product Name: 4-Nitroanthranilic acid
• Synonyms: P-NITROANTHRANILIC ACID;2-amino-4-nitro-benzoicaci;4-nitro-anthranilicaci;4-Nitro-2-aminobenzoic acid;4-NITROANTHRANILIC ACID;2-AMINO-4-NITROBENZOIC ACID;4-NITROANTHRANILIC ACID, TECH., 90%;4-NitroAnthranillicAcid
• CAS NO: 619-17-0
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.13
• EINECS: 210-583-5
• Product Categories: FINE Chemical & INTERMEDIATES;Fluorobenzene;Amines and Anilines;Amino Acids and Derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;API intermediates;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 619-17-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 257 °C (dec.)(lit.)
• Boiling Point: 315.51°C (rough estimate)
• Flash Point: 214.7 °C
• Appearance: Orange/Crystalline Powder
• Density: 1.5181 (rough estimate)
• Vapor Pressure: 3.29E-08mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.92±0.13(Predicted)
• Water Solubility: <0.01 g/100 mL at 22℃
• CAS DataBase Reference: 4-Nitroanthranilic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitroanthranilic acid(619-17-0)
• EPA Substance Registry System: 4-Nitroanthranilic acid(619-17-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: CB3675000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 619-17-0(Hazardous Substances Data)

Usage

Chemical Properties

Orange crystalline powder

Definition

ChEBI: An aminobenzoic acid that is anthranilic acid with a nitro substituent at position 4.

General Description

Orange prisms or orange powder. Sweet taste.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Nitroanthranilic acid is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

Fire Hazard

Flash point data for 4-Nitroanthranilic acid are not available; however, 4-Nitroanthranilic acid is probably combustible.

Purification Methods

Crystallise the acid from water, EtOH (m 271o) or aqueous EtOH (m 269o). The acetyl derivative has m 217o (from EtOH), m 222o (from aqueous EtOH). [Chapman & Stephen J Chem Soc 1796 1925, Beilstein 14 II 234, 14 III 975, 14 IV 1087.]

InChI:InChI=1/C7H6N2O4/c8-6-3-4(9(12)13)1-2-5(6)7(10)11/h1-3H,8H2,(H,10,11)

Synthetic route

diethyl 2,4-dinitrobenzylidenemalonate (87840-68-4) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With diethylamine; tert-butyl alcohol for 48h; Ambient temperature;	75%
With sodium hydrogencarbonate; diethylamine; tert-butyl alcohol Mechanism; 1.) room temp., 48 h, 2.) chloroform;	75%

2,4-dinitrobenzoic acid (610-30-0) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With ferrous(II) sulfate heptahydrate; ammonia In water at 50 - 60℃;	67%

2-chloro-4-nitrobenzoic acid (99-60-5) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Stage #1: 2-chloro-4-nitrobenzoic acid With copper(l) iodide; sodium azide; ethanol; caesium carbonate; N,N`-dimethylethylenediamine at 20 - 95℃; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water pH=2 - 3;	62%

4-nitrophthalic anhydride (5466-84-2) → 2-amino-5-nitro-benzoic acid (616-79-5) + 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With ammonium hydroxide Behandeln des entstandenen Gemisches mit alkal. Natriumhypochlorit-Loesung;

4-nitrophthalic amide (13138-53-9) → 2-amino-5-nitro-benzoic acid (616-79-5) + 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With alkaline aqueous potassium hypobromite

2-acetamido-4-nitrobenzoic acid (951-97-3) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With ethanol; sulfuric acid
With hydrogenchloride; ethanol
With hydrogenchloride
With hydrogenchloride In water for 1h; Reflux;

4-nitro-2-carbamoylbenzoic acid (65911-47-9) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With hydrogenchloride; potassium hydroxide; bromine 1.) heating, 1 h, 2.) 0 deg C; Yield given. Multistep reaction;
With sodium hypochlorite In water at 0 - 30℃; Temperature;

2,4-dinitrotoluene (121-14-2) + benzene (71-43-2) → biphenyl (92-52-4) + 2-amino-4-nitrobenzaldehyde (109466-84-4) + 3-nitro-aniline (99-09-2) + 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
at 343℃; Product distribution; Mechanism; thermolysis in supercritical benzene; other temperature, pressure;	A 100.0 (unit not given) B 35.8 (unit not given) C 20.0 (unit not given) D 22.5 (unit not given)

N-(2-methyl-7-nitro-4-oxo-4H-quinazolin-3-yl)-diacetamide + permanganate → 4-Nitroanthranilic acid (619-17-0)

7-nitro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one (38527-51-4) + alkali → benzoic acid (65-85-0) + 4-Nitroanthranilic acid (619-17-0)

4-nitrophthalimide (89-40-7) + furan-2,3,5(4H)-trione pyridine (1:1) + calcium chloride → 2-amino-5-nitro-benzoic acid (616-79-5) + 4-Nitroanthranilic acid (619-17-0)

<4-nitro-isatoic acid >-anhydride → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With hydrogenchloride; acetic acid

<4-nitro-phthalic acid >-imide → 2-amino-5-nitro-benzoic acid (616-79-5) + 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With sodium hydroxide; calcium chloride Erwaermen der Mischung auf 100grad;

2,4-dinitrotoluene (121-14-2) → meta-dinitrobenzene (99-65-0) + 6-nitro-2,1-benzoisoxazole (15264-44-5) + 2-amino-4-nitrobenzaldehyde (109466-84-4) + 4-Nitroanthranilic acid (619-17-0) + P - NO2 + H

Conditions	Yield
In benzene at 340℃; Product distribution; Kinetics; Rate constant; in sealed tube; other solvent (neat);

4-nitrophthalic amide (13138-53-9) + alkaline aqueous potassium hypobromite → 2-amino-5-nitro-benzoic acid (616-79-5) + 4-Nitroanthranilic acid (619-17-0)

sulfuric acid (7664-93-9) + 4-acetylamino-6-nitro-isophthalic acid (342045-62-9) → 4-amino-2-nitrobenzoic acid (610-36-6) + 4-Nitroanthranilic acid (619-17-0)

4-acetylamino-6-nitro-isophthalic acid (342045-62-9) + alkali → 4-amino-2-nitrobenzoic acid (610-36-6) + 4-Nitroanthranilic acid (619-17-0)

4-amino-2-aminobenzoic acid (611-03-0) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
With Streptomyces thioluteus para-aminobenzoate N-oxygenase

4-nitrophthalimide (89-40-7) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) aq. KOH, 2.) 6 N aq. HCl / 1.) RT, 4 h, 2.) 0 deg C, 90 min 2: 1.) Br2, 1 N aq. KOH, 2.) 2 N aq. HCl / 1.) heating, 1 h, 2.) 0 deg C View Scheme

2,4-dinitrobenzaldehyde (528-75-6) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / pyridine / titanium(IV) chloride / CCl4; tetrahydrofuran / 24 h 2: 75 percent / 1.) t-butyl alcohol, diethylamine, 2.) aq. sodium hydrogen carbonate / 1.) room temp., 48 h, 2.) chloroform View Scheme

N-(2-methyl-5-nitrophenyl)acetamide (2879-79-0) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate 2: alcohol; sulfuric acid View Scheme
Multi-step reaction with 2 steps 1: calcium permanganate 2: concentrated hydrochloric acid; alcohol View Scheme
Multi-step reaction with 2 steps 1: water; potassium permanganate; magnesium sulfate 2: aqueous hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: potassium permanganate / water / 1.5 h / 80 °C 2: hydrogenchloride / water / 1 h / Reflux View Scheme

2-methyl-5-nitroaniline (99-55-8) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 0.25 h 2: potassium permanganate / water / 1.5 h / 80 °C 3: hydrogenchloride / water / 1 h / Reflux View Scheme

phthalic anhydride (85-44-9) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / 0.17 h 1.2: 1 h / 70 °C 2.1: acetic anhydride / 2 h / 90 - 120 °C 3.1: 5 - 70 °C 4.1: sodium hypochlorite / water / 0 - 30 °C View Scheme

4-nitrophthalic acid (610-27-5) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic anhydride / 2 h / 90 - 120 °C 2: 5 - 70 °C 3: sodium hypochlorite / water / 0 - 30 °C View Scheme

4-nitrophthalic anhydride (5466-84-2) → 4-Nitroanthranilic acid (619-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 - 70 °C 2: sodium hypochlorite / water / 0 - 30 °C View Scheme

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 4-Nitroanthranilic acid (619-17-0) → (E)-methyl 2-([(dimethylamino)methylene]amino)-4-nitrobenzoate (113290-38-3)

Conditions	Yield
In N,N-dimethyl-formamide Heating;	99%
In N,N-dimethyl-formamide at 105℃; for 0.25h; Microwave irradiation;	92%

propionic acid anhydride (123-62-6) + 4-Nitroanthranilic acid (619-17-0) → 2-Ethyl-7-nitro-benzo[d][1,3]oxazin-4-one

Conditions	Yield
for 1h; Heating;	98.2%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + 4-Nitroanthranilic acid (619-17-0) → 7-nitroquinazolin-4(3H)-one (20872-93-9)

Conditions	Yield
In neat (no solvent) at 150℃; Sealed tube;	95%
at 160℃; for 12h; Inert atmosphere;	93%
at 160℃;	93%

4-Nitroanthranilic acid (619-17-0) → 7-nitroquinazolin-4-one (20872-93-9)

Conditions	Yield
With formamide In water	95%

diaminoglyoxime (2580-79-2) + 4-Nitroanthranilic acid (619-17-0) → N'-hydroxy-7-nitro-4-oxo-3,4-dihydroquinazoline-2-carboximidamide (1446556-87-1)

Conditions	Yield
With acetic acid for 0.5h; Reflux;	95%

1,1-dimethoxyethane (534-15-6) + 4-Nitroanthranilic acid (619-17-0) → methyl 2-amino-4-nitrobenzoate (3558-19-8)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.25h; Inert atmosphere; Microwave irradiation;	95%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + 4-Nitroanthranilic acid (619-17-0) → 7-nitroquinazolin-4-one (20872-93-9)

Conditions	Yield
In water at 165℃; for 4h;	95%

methyl (N-(4-methylphenyl))dithiocarbamate (13037-22-4) + 4-Nitroanthranilic acid (619-17-0) → 7-Nitro-2-thioxo-3-p-tolyl-2,3-dihydro-1H-quinazolin-4-one (81066-88-8)

Conditions	Yield
In N,N-dimethyl-formamide for 6h; Heating;	93%

formamidine acetic acid (3473-63-0) + 4-Nitroanthranilic acid (619-17-0) → 7-nitroquinazolin-4(3H)-one (20872-93-9)

Conditions	Yield
In 2-methoxy-ethanol at 130℃; for 18h;	93%
In 2-methoxy-ethanol at 130℃; for 18h;	84%
for 24h; Reflux;	73.3%
In ethanol Reflux;

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 4-Nitroanthranilic acid (619-17-0) → methyl 2-amino-4-nitrobenzoate (3558-19-8)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide dimethyl acetal; 4-Nitroanthranilic acid In N,N-dimethyl-formamide at 105℃; for 0.25h; Microwave irradiation; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; pH=2; Microwave irradiation;	93%
Stage #1: N,N-dimethyl-formamide dimethyl acetal; 4-Nitroanthranilic acid In ethyl acetate at 100℃; for 0.25h; Sealed tube; Microwave irradiation; Green chemistry; Stage #2: With hydrogenchloride In water; ethyl acetate at 60 - 100℃; for 0.5h; Sealed tube; Microwave irradiation; Green chemistry;	88%

acetic anhydride (108-24-7) + 4-Nitroanthranilic acid (619-17-0) → 2-acetamido-4-nitrobenzoic acid (951-97-3)

Conditions	Yield
In pyridine Ambient temperature;	92.1%
Behandeln des Reaktionsproduktes mit Wasser;

urea (57-13-6) + 4-Nitroanthranilic acid (619-17-0) → 7-nitro-1,2,3,4-tetrahydro-quinazoline-2,4-dione (174565-63-0)

Conditions	Yield
at 160℃; for 6h;	91%
at 160℃; for 6h;	90%

methanol (67-56-1) + 4-Nitroanthranilic acid (619-17-0) → methyl 2-amino-4-nitrobenzoate (3558-19-8)

Conditions	Yield
With sulfuric acid at 75℃; for 72h;	91%
Stage #1: methanol; 4-Nitroanthranilic acid With sulfuric acid for 48h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water	90%
With thionyl chloride Heating / reflux;	88%

bis(trichloromethyl) carbonate (32315-10-9) + 4-Nitroanthranilic acid (619-17-0) → 4-nitroisatoic anhydride (63480-10-4)

Conditions	Yield
In tetrahydrofuran at 70℃; for 12h;	91%
In water at 0℃; for 5h; Inert atmosphere; Large scale;	88%
In 1,4-dioxane for 6h; Heating;	45%

4-Nitroanthranilic acid (619-17-0) → (2-Amino-4-nitrophenyl)methan-1-ol (78468-34-5)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 30℃; for 1h; Inert atmosphere;	91%
Stage #1: 4-Nitroanthranilic acid With diborane In tetrahydrofuran at 65℃; Stage #2: With hydrogenchloride In tetrahydrofuran at 65℃;	82%
With borane-THF In tetrahydrofuran at 20℃; for 12h;	70%

propylamine (107-10-8) + 4-Nitroanthranilic acid (619-17-0) → N-propyl-2-amino-4-nitrobenzamide (1414782-00-5)

Conditions	Yield
Stage #1: 4-Nitroanthranilic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 1h; Stage #2: propylamine In tetrahydrofuran; dichloromethane at 25℃; for 12h;	91%

1,1-dichloro-2-nitro ethylene (6061-04-7) + 4-Nitroanthranilic acid (619-17-0) → 4-nitro-2-(2-nitroacetamido)benzoic acid

Conditions	Yield
In water at 50℃; for 45h; Green chemistry;	91%

triethoxymethylbenzene (1663-61-2) + 4-Nitroanthranilic acid (619-17-0) → 7-nitro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one (38527-51-4)

Conditions	Yield
at 100℃; for 2h; Microwave irradiation; Inert atmosphere;	91%

4-Nitroanthranilic acid (619-17-0) → 2-azido-4-nitrobenzoic acid (78072-75-0)

Conditions	Yield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 20℃; for 2h;	90%
With sodium azide; sodium carbonate; sodium nitrite 1.) H2O, 2.) H2O, r.t., 2 h; Yield given. Multistep reaction;

1,1'-carbonyldiimidazole (530-62-1) + 4-Nitroanthranilic acid (619-17-0) → 4-nitroisatoic anhydride (63480-10-4)

Conditions	Yield
In tetrahydrofuran at 10℃; for 2h; Inert atmosphere;	90%
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

BARBITURIC ACID (67-52-7) + orthoformic acid triethyl ester (122-51-0) + 4-Nitroanthranilic acid (619-17-0) → 4-nitro-2-{[(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}benzoic acid

Conditions	Yield
In iso-butanol Reflux;	90%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + orthoformic acid triethyl ester (122-51-0) + 4-Nitroanthranilic acid (619-17-0) → 2-{[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}-4-nitrobenzoic acid

Conditions	Yield
In iso-butanol Reflux;	90%

triethoxymethylbenzene (1663-61-2) + 4-Nitroanthranilic acid (619-17-0) → (±)-2-ethoxy-7-nitro-2-phenyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
With acetic acid at 100℃; for 24h; Inert atmosphere;	90%

butanoic acid anhydride (106-31-0) + 4-Nitroanthranilic acid (619-17-0) → 7-Nitro-2-propyl-benzo[d][1,3]oxazin-4-one

Conditions	Yield
for 1h; Heating;	89.3%

all-trans-Retinal (116-31-4) + 4-Nitroanthranilic acid (619-17-0) → 2-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-4-nitro-benzoic acid (144459-79-0)

Conditions	Yield
In methanol; dichloromethane for 2h; Ambient temperature;	89%

formamidine acetic acid (3473-63-0) + 4-Nitroanthranilic acid (619-17-0) → 4-hydroxy-7-nitroquinazoline (20872-93-9)

Conditions	Yield
In ethanol for 5h; Reflux;	89%

aminoferrocene (1273-82-1) + 4-Nitroanthranilic acid (619-17-0) → N-(ferrocenylmethyl)-2-amino-4-nitrobenzamide

Conditions	Yield
Stage #1: 4-Nitroanthranilic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 1h; Stage #2: aminoferrocene In tetrahydrofuran; dichloromethane at 25℃; for 12h;	89%

methyl thioisocyanate (556-61-6) + 4-Nitroanthranilic acid (619-17-0) → 3-methyl-7-nitro-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (926218-64-6)

Conditions	Yield
With triethylamine	89%
With triethylamine In ethanol for 6h; Reflux;	89%
With acetic acid at 160℃; for 24h;	11.4 g

4-Nitroanthranilic acid (619-17-0) → 2-iodo-4-nitrobenzoic acid (89459-38-1)

Conditions	Yield
Stage #1: 4-Nitroanthranilic acid With toluene-4-sulfonic acid In water for 0.05h; Stage #2: With sodium nitrite In water for 0.25h; Stage #3: With potassium iodide In water	88%
Stage #1: 4-Nitroanthranilic acid With sulfuric acid at 0℃; for 1h; Stage #2: With sodium nitrite In water at 0℃; for 1h; Stage #3: With potassium iodide In water at 0 - 60℃; for 4h;	68%
With sulfuric acid; potassium iodide; sodium nitrite In water at 0 - 60℃; for 6h;	68%

4-Nitroanthranilic acid (619-17-0) + Triethyl orthopropionate (115-80-0) → (±)-2-ethoxy-2-ethyl-7-nitro-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
at 100℃; for 1.5h; Time; Microwave irradiation; Inert atmosphere;	88%

Upstream product

• 951-97-3 2-acetamido-4-nitrobenzoic acid 
• 65911-47-9 4-nitro-2-carbamoylbenzoic acid 
• 121-14-2 2,4-dinitrotoluene 
• 71-43-2 benzene 
• 38527-51-4 7-nitro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one 
• 89-40-7 4-nitrophthalimide 
• 13138-53-9 4-nitrophthalic amide 
• 7664-93-9 sulfuric acid 
• 342045-62-9 4-acetylamino-6-nitro-isophthalic acid 
• 5466-84-2 4-nitrophthalic anhydride 
• 610-27-5 4-nitrophthalic acid 
• 85-44-9 phthalic anhydride 
• 99-55-8 2-methyl-5-nitroaniline 
• 610-30-0 2,4-dinitrobenzoic acid 

Downstream Products

• 108302-73-4 2-[(carboxymethyl)amino]-4-nitrobenzoic acid 
• 83848-59-3 5-nitroquinoline-8-carboxylic acid 
• 174565-63-0 7-nitro-1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 3558-19-8 methyl 2-amino-4-nitrobenzoate 
• 55204-24-5 ethyl 2-amino-4-nitrobenzoate 
• 3698-54-2 2,3,4,6-tetranitroaniline 
• 611-03-0 4-amino-2-aminobenzoic acid 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 72517-19-2 2,3-dihydroxy-4-nitrobenzoic acid 
• 89459-38-1 4-nitro-2-iodobenzoic acid 
• 725246-85-5 2-hydrazino-4-nitro-benzoic acid 
• 78334-06-2 4-amino-2-mercapto-benzoic acid 
• 860689-09-4 6-carboxy-2-hydroxy-3-nitro-benzenediazonium-betaine 
• 99-09-2 3-nitro-aniline 

Relevant articles and documents

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Functionalization of quinazolin-4-ones part 1: Synthesis of novel 7-substituted-2-thioxo quinazolin-4-ones from 4-substituted-2-aminobenzoic acids and PPh3(SCN)2

4-(Nitro, amino, acetylamino)-2-aminobenzoic acid were allowed to react with PPh3(SCN)2 and gave the crossholding 7-nitro, 7-acetylamino- and 7-amino-2-thioxo quinazolin-4-ones respectively. The nature of the substituent at position 4 of the 2-aminobenzoic acids has significant influence on the outcome of the cyclisation reaction with PPh 3(SCN)2. Similarly, the nature of the substituent at position 7 of the 2-substituted quinazolin-4-ones significantly affected the ease with which alkylation reactions could be performed. The alkylation selectivity of the 7- substiuted-2-thioxo quinazolin-4-ones was found to depend on the nature of the alkyl halide and the nature of the substituent at position 2.

Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source

A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.