30652-11-0

Basic information

• Product Name: 3-HYDROXY-1,2-DIMETHYL-4(1H)-PYRIDONE
• Synonyms: L1;DMHP;DEFERIDONE;DEFERIPRON;DEFERIPRONE;CP20;3-HYDROXY-1,2-DIMETHYL-4(1H)PYRIDINONE;3-HYDROXY-1,2-DIMETHYL-4(1H)-PYRIDONE
• CAS NO: 30652-11-0
• Molecular Formula: C₇H₉NO₂
• Molecular Weight: 139.15
• EINECS: 212-783-8
• Product Categories: API intermediates;Chelating Agents, Ligands;Chelating Agents & Ligands;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Heterocyclic Building Blocks;Piperidones;Heterocycles
• Mol File: 30652-11-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 272-275 °C(lit.)
• Boiling Point: 255.1°C (rough estimate)
• Flash Point: 94.5 °C
• Appearance: White to off-white/Crystalline Powder or Needles
• Density: 1.1997 (rough estimate)
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in Water (up to 5 mg/ml with warming).
• PKA: pKa1 3.3, pKa2 9.7(at 25℃)
• Water Solubility: Soluble in hot water
• Stability: Stable for 1 year from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily.
• Merck: 14,2859
• CAS DataBase Reference: 3-HYDROXY-1,2-DIMETHYL-4(1H)-PYRIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-1,2-DIMETHYL-4(1H)-PYRIDONE(30652-11-0)
• EPA Substance Registry System: 3-HYDROXY-1,2-DIMETHYL-4(1H)-PYRIDONE(30652-11-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: UU7785940
• Hazardous Substances Data: 30652-11-0(Hazardous Substances Data)

Usage

Description

Deferiprone, the first oral iron chelator, was marketed in India for the management of thalassaemia. Patients with thalassaemia, a blood related genetic disorder, require life time transfusion which causes excessive deposition of iron in liver and spleen, subsequent damage to organs and eventually death unless iron is removed by a chelator. Deferiprone is a potent iron chelator that mobilizes excessive iron from iron storage proteins ferritin and hemosiderin, from iron saturated transferrin and lactoferrin, but not from hemoglobin. The deferiprone-iron complex is excreted in urine and bile. Deferiprone was reportedly well accepted by patients and no hematological toxicity was observed. Deferiprone has also been demonstrated as an effective and safe chelator in the mobilization of aluminum.

Chemical Properties

White Needles

Originator

Cipla (India)

Uses

Different sources of media describe the Uses of 30652-11-0 differently. You can refer to the following data:
1. 3-Hydroxy-1,2-dimethyl-4(1H)-pyridone (OH-pyridone) may be used in the bacterial killing assays. It has been employed as hydroxyketone chelating agent and its cytotoxic action against oral human normal and tumor cell lines has been evaluated.
2. iron chelating agent
3. A chelator that could replace disferrioxamine. It is orally and parenterally effective in the removal of iron in vivo from rabbits and mice and also from transferrin and ferritin in vitro

Definition

ChEBI: A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.

Brand name

Kelfer

General Description

3-Hydroxy-1,2-dimethyl-4(1H)-pyridone (Hdpp, Deferiprone) is a hydroxy ketone derivative. It reacts with uranyl salts [UO2(NO3)2] in aqueous acidic solution to afford mono nuclear complexes ([UO2(dpp)(Hdpp)2(H2O)]ClO4). X-ray studies have been conducted to examine the structure and geometry of these complexes.

Clinical Use

Orally administered chelator:Treatment of transfusional iron overload

Drug interactions

Potentially hazardous interactions with other drugsNone known.

Metabolism

Deferiprone is hepatically metabolised to an inactive glucuronide metabolite and is excreted mainly in the urine as the metabolite and the iron-deferiprone complex, with a small amount of unchanged drug.

References

1) Hider and Hoffbrand (2018),?The Role of Deferiprone in Iron Chelation; N. Engl. J. Med.,?379?2140 2) Sripetchwandee?et al.?(2016),?A combination of an iron chelator with an antioxidant effectively diminishes the dendritic loss, tau-hyperphosphorylation, amyloid-β accumulation and brain mitochondrial dynamic disruption in rats with chronic iron-overload., Neuroscience?332?191 3) Liu?et al.?(2018),?Iron and Alzheimer’s Disease: From Pathogenesis to Therapeutic Implications;?Front. Neurosci,?12?632

InChI:InChI=1/C7H9NO2/c1-5-6(9)3-4-8(2)7(5)10/h3-4,10H,1-2H3

Synthetic route

1,2-dimethyl-3-(benzyloxy)-4(1H)-pyridinone (90037-22-2) → deferiprone (30652-11-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 2h;	80%
With hydrogen; palladium on activated charcoal In tetrahydrofuran under ambient conditions;	65%
With concentrated hydrobromic acid

Maltol (118-71-8) + methylamine (74-89-5) → deferiprone (30652-11-0)

Conditions	Yield
In water for 10h; Reflux;	69%
In water at 160 - 162℃; under 6750.5 Torr; for 0.0216667h; Irradiation;	65%
In water for 6.5h; Heating;	60%

isomaltol (3420-59-5) + methylamine (74-89-5) → deferiprone (30652-11-0)

Conditions	Yield
In water for 20h; Heating;	64%

3-(β-D-galactopyranosyloxy)-2-furanyl methyl ketone (82756-28-3) + methylamine (74-89-5) → deferiprone (30652-11-0)

Conditions	Yield
In water for 20h; Heating;	49%

Maltol (118-71-8) + methylamine hydrochloride (593-51-1) → deferiprone (30652-11-0)

Conditions	Yield
With potassium hydroxide In water at 50℃;	25%

deferiprone (30652-11-0) + [(hydrotris(3,5-phenylmethylpyrazolyl)borato)CoCl] → [(hydrotris(3,5-phenylmethylpyrazolyl)borato)Co(3,4-HOPO)]

Conditions	Yield
With (C2H5)3N In methanol; dichloromethane (C2H5)3N added to a soln. of Co complex, a soln. of ligand in MeOH added, stirred at room temp. overnight under N2; evapd. (vac.), dissolved in C6H6, filtered, crystd. by diffusion of the soln. with pentane; elem. anal.;	98%

deferiprone (30652-11-0) + bismuth (III) nitrate pentahydrate + terephthalic acid (100-21-0) + water (7732-18-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [Bi2(1,4-benzenedicarboxylate)(deferiprone-H)4(H2O)2]·2DMF

Conditions	Yield
at 100℃; for 72h; Sealed tube; High pressure;	98%

deferiprone (30652-11-0) + water (7732-18-5) + tantalum pentaethoxide (150747-55-0) → tris(1,2-dimethyl-3-hydroxy-4(1H)-pyridone)oxotantalum

Conditions	Yield
In methanol; water addn. of soln. of tantalum compd. in methanol to soln. of deferiprone inmethanol, stirring at room temp. overnight, addn. of water, stirring fo r 30 min; evapn. at 40°C, washing with warm CHCl3, filtration, drying in vac., elem. anal.;	97%

dichloro(mesitylene)ruthenium(II) dimer + deferiprone (30652-11-0) → [RuCl(C7H8NO2)(C6H3(CH3)3)] (176792-83-9)

Conditions	Yield
With NaOCH3 In methanol; water byproducts: NaCl; (N2); reflux (3 h); solvent removal, dissoln. (CH2Cl2), filtration (Celite), evapn.; elem. anal.;	93%

deferiprone (30652-11-0) + methyl trifluoromethanesulfonate (333-27-7) → Trifluoro-methanesulfonate3-hydroxy-4-methoxy-1,2-dimethyl-pyridinium;

Conditions	Yield
In chloroform for 3h; Heating;	90%

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer + deferiprone (30652-11-0) + sodium methylate (124-41-4) → Rh(C5(CH3)5)Cl(C5H2NO2(CH3)2) (173413-67-7)

Conditions	Yield
In methanol byproducts: NaCl; N2-atmosphere; stoich. amts., refluxing for 3 h; solvent removal, extn. into CH2Cl2, filtration (Celite), evapn., recrystn. (CH2Cl2/Et2O);	90%

deferiprone (30652-11-0) + zinc(II) chloride (7646-85-7) → bis-(3-hydroxy-1,2-dimethyl-4-pyridinonato)zinc(II)

Conditions	Yield
With NaOH In methanol; water raising of the pH to 7 with dilute NaOH, concn.,; cooling, filtration, elem. anal.;	90%

deferiprone (30652-11-0) + 2,5-dihydroxybenzoic acid. (490-79-9) → C7H6O4*C7H9NO2

Conditions	Yield
In ethanol; acetone at 60℃; for 2h;	90%
In ethanol; acetone at 20 - 45℃; for 73.7h; Sealed tube;	36.5 mg

deferiprone (30652-11-0) + 4-hydroxy-benzoic acid (99-96-7) → C7H6O3*C7H9NO2

Conditions	Yield
In water at 60℃; for 2h;	90%

deferiprone (30652-11-0) + vanadyl (20644-97-7) → bis(1,2-dimethyl-3-hydroxy-4-pyridinonato)oxidovanadium(IV)

Conditions	Yield
With NaOH In water under Ar; ligand suspended in water; heated at 50-60°C; VO(2+) soln. and solid NaOH added; chilled; filtered; solid washed with water and acetone; dried in vac.; elem. anal.;	86%

deferiprone (30652-11-0) + p-toluenesulfonyl chloride (98-59-9) → 1,2-dimethyl-4-oxo-1,4-dihydropyridin-3-yl 4-methylbenzenesulfonate (1259401-68-7)

Conditions	Yield
With pyridine at 20℃; Inert atmosphere;	86%

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer + deferiprone (30652-11-0) → Rh(C5(CH3)5)Cl(C5H2NO2(CH3)2) (173413-67-7)

Conditions	Yield
	85%

deferiprone (30652-11-0) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) → [(p-cymene)Ru(C7H8NO2)Cl] (252573-94-7)

Conditions	Yield
With NaOMe In methanol; dichloromethane addn. of 1 equiv. NaOMe (in MeOH) to ligand (in CH2Cl2), addn. to stoich. amt. of metal complex (in CH2Cl2), standing for 2 h; solvent removal (vac.), extn. into Et2O/CH2Cl2=1:2, evapn. (reduced pressur), drying (vac.); elem. anal.;	85%

chloro(1,5-cyclooctadiene)iridium(I) dimer + deferiprone (30652-11-0) → [Ir(C8H12)(CH3NCHCHCOCOC(CH3))]*0.5H2O

Conditions	Yield
With MeONa In methanol; dichloromethane inert atm.; 4 h; evapn. (vac.), extraction (Et2O/CH2Cl2 1:2), evapn., drying (vac.); elem. anal.;	85%

deferiprone (30652-11-0) + manganese (II) acetate tetrahydrate (6156-78-1) → Mn(1,2-dimethyl-3-hydroxy-4-pyridinone(1-))3*2.5H2O

Conditions	Yield
With sodium acetate trihydrate In methanol to soln. ligand and AcONa*3H2O in MeOH Mn(OAc)2*4H2O was added and refluxed for 4 h; react. mixt. was cooled to room temp., ppt. was filtered, washed with Et2O and dried in vacuo overnight; elem. anal.;	84.6%

deferiprone (30652-11-0) + chromium chloride hexahydrate → fac-Cr(III)(3-oxy-2-methyl-4-pyridinone)3*2H2O

Conditions	Yield
With triethylamine In methanol CrCl3*6H2O added to soln. of deferiprone and triethylamine in CH3OH, mixt. refluxed for 4 h, cooled to room temp.; solid filtered off, washed with cold methanol and ether, dried under vac., recrystd. from water; elem. anal.;	84.4%

deferiprone (30652-11-0) + vanadyl sulfate *3.6H2O → bis(1,4-dihydro-1,2-dimethyl-4-oxo-3-pyridinolato)oxovanadium (IV) (186321-59-5, 175662-51-8)

Conditions	Yield
With potassium hydroxide In water to a soln. of 1-hydroxy-4,6-dimethyl-2(1H)-pyrimidinone in water added dropwise a soln. of VOSO4*3.6H2O in water, pH of the soln. adjusted to 10with 2M KOH, stirred overnight; precipitate collected by filtration, washed several times with H2O, dried over anhydrous P2O5 in vacuo, elem. anal.;	84%

deferiprone (30652-11-0) + manganese(ll) chloride → Mn(1,2-dimethyl-3-hydroxy-4-pyridinone(1-))2Cl*0.25H2O

Conditions	Yield
With triethylamine In acetonitrile to soln. ligand and Et3N in MeCN MnCl2 was added and refluxed for 6 h; react. mixt. was cooled to room temp. and concd. in vacuo, cold Et2O wasadded, ppt. was filtered, washed with Et2O and dried in vacuo overnight ; elem. anal.;	83.8%

methanol (67-56-1) + deferiprone (30652-11-0) → 1,2-dimethyl-2-methoxy-1,2-dihydro-pyridine-3,4-dione

Conditions	Yield
With silver(l) oxide at 45℃; for 2h;	83%

vanadyl sulfate trihydrate + deferiprone (30652-11-0) → bis(1,2-dimethyl-3-hydroxy-4-pyridinonato)oxidovanadium(IV)

Conditions	Yield
With KOH In water under aerobic conditions; VOSO4*3H2O in hot water added slowly to suspn.of ligand (molar ratio 1:2) in hot water; aq. soln. of KOH (2 equiv.) a dded (pH ca. 3); refluxed for 2 h; ppt. collected; washed with acetone; dried overnight in vac.; satisfactory elem. anal.;	83%

deferiprone (30652-11-0) + tetracarbonyldi-μ-chlorodirhodium(I) → [Rh(CO)2(CH3NCHCHCOCOC(CH3))] (250638-50-7)

Conditions	Yield
With MeONa In methanol; dichloromethane 4 h; evapn. (vac.), extraction (Et2O/CH2Cl2 1:2), evapn., drying (vac.); elem. anal.;	83%

deferiprone (30652-11-0) + di-μ-chlorobis{2-[(dimethylamino)methyl]phenyl-C,N}dipalladium (II) → [Pd(CH3NCHCHCOCOC(CH3))((CH3)2NCH2C6H4)] (250717-07-8, 250638-60-9)

Conditions	Yield
With NaOMe In methanol; dichloromethane 2 h; evapn. (vac.), extraction (Et2O/CH2Cl2), evapn., drying (vac., 50°C); elem. anal.;	83%

deferiprone (30652-11-0) + water (7732-18-5) + manganese(ll) chloride → Mn(1,2-dimethyl-3-hydroxy-4-pyridinone(1-))2(H2O)2*0.5H2O

Conditions	Yield
With triethylamine In acetonitrile under N2 atm. to slurry MnCl2 in MeCN was added soln. ligand and Et3N inMeCN, mixt. was refluxed for overnight; soln. was cooled to room temp., volume was reduced by stream N2 gas, cold Et2O was added, solid was filtered, washed with MeCN, Et2O, dried under vac. overnight; elem. anal.;	83%

deferiprone (30652-11-0) + zinc(II) nitrate hexahydrate + terephthalic acid (100-21-0) + water (7732-18-5) → 3Zn(2+)*2C8H4O4(2-)*2C7H8NO2(1-)*2H2O

Conditions	Yield
In ethanol at 95℃; for 24h;	82%

methanol (67-56-1) + beryllium(II) sulphate tetrahydrate + deferiprone (30652-11-0) → Be(dpp)2*MeOH (449141-30-4)

Conditions	Yield
With NH3 In water 3-hydroxy-1,2-dimethyl-4-pyridinone was added to BeSO4*4H2O in water, after dissolution pH was adjusted to 8.5 with concd. NH3; solvent was evapd. at 323-333 K and cooled to room temp., ppt. was filtered off, washed with cold water, and dried in air, recrystn. from MeOH/Et2O; elem. anal.;	81%

deferiprone (30652-11-0) + dichlorobis(triethylphosphine)-μ-dichlorodipalladium(II) → [PdCl(CH3NCHCHCOCOC(CH3))(P(C2H5)3)]*0.5H2O

Conditions	Yield
With NaOMe In methanol; dichloromethane 2 h; evapn. (vac.), extraction (Et2O/CH2Cl2), evapn., drying (vac., 50°C); elem. anal.;	80%

deferiprone (30652-11-0) + uranyl nirate hexahydrate + sodium perchlorate → [UO2(3-oxy-1,2-dimethyl-4(1H)-pyridone)2(H2O)]

Conditions	Yield
In water slow evapn. of aq. soln. of 0.1 M NaClO4, pyridone-compound, uranyl-compound at room temp. at pH 3; elem. anal.;	80%

deferiprone (30652-11-0) + trans-di-μ-chloro-bis[chloro(tributylphosphine)palladium] → [PdCl(CH3NCHCHCOCOC(CH3))(P(C4H9)3)] (250638-59-6)

Conditions	Yield
With NaOMe In methanol; dichloromethane inert atm.; 2 h; evapn. (vac.), extraction (Et2O/CH2Cl2), evapn., drying (vac., 50°C); elem. anal.;	78%

deferiprone (30652-11-0) + zinc(II) nitrate hexahydrate + terephthalic acid (100-21-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3Zn(2+)*2C8H4O4(2-)*2C7H8NO2(1-)*2C3H7NO

Conditions	Yield
at 100℃; for 24h;	77%

Upstream product

• 30651-70-8 (3E,5E)-4,5-diethylocta-3,5-diene 
• 30651-68-4 (5E,7E)-5,7-Dodecadiene 
• 30651-62-8 1-Piperazinamine,N-(phenylmethylene)-(9CI) 
• 30651-61-7 4-benzyl-2,6-dimethyl-piperazin-1-amine 
• 30651-60-6 1-AMINO PIPERAZINE 
• 30651-43-5 (S)-S-(2-amino-2-carboxyethyl)-D-homocysteine 
• 30651-34-4 (2S)-2-({9-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}amino)butanedioic acid (non-preferred name) 
• 30651-24-2 5-Nitropyridine-2-carboxylic acid 
• 30651-03-7 pentacyclo[7.3.1.1~4,12~.0~2,7~.0~6,11~]tetradecan-4-ol (non-preferred name) 
• 30650-95-4 N-(1-Adamantyl)-4-(dimethylamino)butyramide 
• 30650-90-9 ETHYL 3-METHYL-4-NITROBENZOATE 
• 30650-47-6 sodium (4-hydroxyphenyl)[(3-methoxy-1-methyl-3-oxoprop-1-enyl)amino]acetate 
• 30650-28-3 2-{2-[2-(biphenyl-4-yl)ethenyl]-5-nitro-1H-imidazol-1-yl}ethyl 4-methylbenzenesulfonate 
• 30650-24-9 5-amino-N,N-dimethyl-2-(prop-2-en-1-yloxy)benzamide hydrochloride (1:1) 

Downstream Products

• 30652-12-1 1-Ethyl-3-hydroxy-2-methyl-4(1H)-pyridinone 
• 30652-13-2 1-propyl-2-methyl-3-hydroxypyrid-4-one 
• 30652-15-4 1-Butyl-2-methyl-3-hydroxy-4(1H)-pyridinone 
• 30652-17-6 3-hydroxy-2-methyl-1-pentylpyridin-4(1H)-one 
• 30652-21-2 3-Hydroxy-1-(2-hydroxyethyl)-2-methyl-4(1H)-pyridinone 
• 3065-23-4 2,4,5-trichlorophenyl N-[(benzyloxy)carbonyl]-L-valinate 
• 306-52-5 triclofos 
• 3065-27-8 2,4,5-trichlorophenyl 3-phenyl-N-[(phenylmethoxy)carbonyl]-L-alaninate 
• 30652-87-0 Amphotericin β 
• 3065-29-0 N,O-Bis[(benzyloxy)carbonyl]-L-tyrosine 2,4,5-trichlorophenyl ester 
• 30653-05-5 Bis-[2-hydroxy-5-methyl-3-(benzotriazol-2-yl)-phenyl]-methane 
• 30653-26-0 Estra-1,3,5(10)-triene-3,15,16,17-tetrol,(15a,16a,17b)- 
• 30653-58-8 5-amino-N-butyl-4-chloro-2-(prop-2-en-1-yloxy)benzamide 
• 306-53-6 azamethonium bromide 

Recommend Products

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• 3420-59-5  isomaltol 
• 593-51-1  methylamine hydrochloride 
• 7439-89-6  iron(II) 
• 1219438-80-8  3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-1,2-dimethyl-4(1H)-pyridinone 
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• 490-79-9  2,5-dihydroxybenzoic acid. 
• 10312-55-7  3-aminoterephthalic acid 
• 7732-18-5  water