58-56-0

Basic information

• Product Name: Pyridoxine hydrochloride
• Synonyms: campoviton6;hexabetalin;hexa-betalin(r);hexabionehydrochloride;hexavibex;hexermin;hexobion;paxadon
• CAS NO: 58-56-0
• Molecular Formula: C₈H₁₂NO₃*Cl
• Molecular Weight: 205.64
• EINECS: 200-386-2
• Product Categories: Biochemistry;Pyridinium Compounds;Vitamins;Nutritional Supplements;Vitamins and derivatives;Aromatics;Heterocycles;Vitamin Ingredients;Vitamin series;Isolabel;vitamin;Inhibitors
• Mol File: 58-56-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 214-215 °C(lit.)
• Boiling Point: 491.9 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: White to almost white/Crystalline Powder
• Density: 1.2784 (rough estimate)
• Vapor Density: 7.1 (vs air)
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 g/mL at 20 °C, clear, colorless
• Water Solubility: 0.1 g/mL (20 ºC)
• Sensitive: Light Sensitive
• Stability: Stable. Protect from air and light.
• Merck: 14,7982
• BRN: 3632435
• CAS DataBase Reference: Pyridoxine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridoxine hydrochloride(58-56-0)
• EPA Substance Registry System: Pyridoxine hydrochloride(58-56-0)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-37/39-45-36/37-16-7-24/25
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 2
• RTECS: UV1350000
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 58-56-0(Hazardous Substances Data)

Usage

Nutrition supplements

Pyridoxine hydrochloride is the hydrochloride salt of Vitamin B6. Vitamin B6 (B6) is a water-soluble vitamin, which can be found in various foods such as fish, poultry, whole grains, legumes, banana, nuts, and sesame.Vitamin B6 has an important role in the metabolism of amino acids as a coenzyme, pyridoxal 5'-phosphate.? B6 may exert an anticolon tumor effect by the protection of the colon epithelium from damage in rats treated with 1,2-dimethylhidrazine (DMH) and to decreased lithocholic acid, a colon carcinogen. Vitamin B6 may prevent such diseases by lowering inflammation.

Chemical Properties

White or almost white, crystalline powder.

Uses

Pyridoxine is one of the vitamins of the B6 complex; present in many foodstuffs (yeast, liver and cereals). Pyridoxine has a role in transporting protein Bsu1, Pyridoxine contributes to thiamine uptak e; characterization of thiamine (vitamin B1) transporter Thi9 from Schizosaccharomyces pombe.

Uses

Pyridoxine Hydrochloride is an acid form of vitamin b6, a water- soluble vitamin. it is soluble in water, and slightly soluble in alco- hol. it is slowly affected by sunlight and is reasonably stable in air. it has a ph of 2.3–3.5. it is also termed vitamin b6 hydrochloride. see pyridoxine.

Definition

ChEBI: Pyridoxine hydrochloride is the hydrochloride salt of pyridoxine. It is a hydrochloride and a vitamin B6. It contains a pyridoxine.

Brand name

Hexa-Betalin (Lilly).

General Description

Vitamin B6 has six forms namely, pyridoxal, pyridoxine, pyridoxamine, pyridoxamine 5′-phosphate, pyridoxine 5′-phosphate and pyridoxal 5′-phosphate. Pyridoxine is a is a water-soluble vitamin and a pyrimidine derivative of vitamin B6. It is considered heat and acid stable.

Biochem/physiol Actions

Vitamin B6 is an essential coenzyme for amino acid, carbohydrate and lipid metabolism. Pyridoxine serves as a primary source in multivitamins. Pyridoxine deficiency is associated with peripheral neuropathy.

Clinical Use

Vitamin B6

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, intramuscular, and subcutaneous routes. Human reproductive effects by ingestion and intramuscular routes: postpartum changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Pyridoxine is metabolised to its active form pyridoxamine phosphate. It is stored mainly in the liver where there is oxidation to 4-pyridoxic acid and other inactive metabolites which are excreted in the urine.

Purification Methods

Purify the vitamin by recrystallisation from EtOH/Me2CO, n-BuOH or MeOH/Et2O. Its solubility in H2O is 22%, and in EtOH it is 1.1%. It is insoluble in Et2O and CHCl3. Acidic aqueous solutions are stable at 120o/30minute. The free base has m 159-160o after recrystallisation from Me2CO and sublimation at 140-145o/0.0001mm. It has UV max at 290nm ( 84,000), 253 and 325nm ( 3,700 and 7,100) in 0.1N aqueous HCl. [Khua & Wendt Chem Ber 71 780 1938, 72 311 1939, Harris & Folkers J Am Chem Soc 61 1242 1939, Harris et al. J Am Chem Soc 62 3198 1940, Beilstein 21/5 V 492.]

InChI:InChI=1/C8H11NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,10-12H,3-4H2,1H3;1H/p-1

Synthetic route

pyridoxine triacetate (10030-93-0) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride In water for 2h; Heating;	98%
With hydrogenchloride; water for 2h; Heating / reflux;	72%

5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid diethyl ester (2397-71-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid diethyl ester With sodium tetrahydroborate; iron(II) sulfate; N,N-dimethyl-aniline In tetrahydrofuran for 4h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; Reagent/catalyst; Solvent;	93.4%

4,5-dihydroxymethyl-2-methyl-2-cyclopentenone → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 4,5-dihydroxymethyl-2-methyl-2-cyclopentenone With ozone In methanol; water at -30℃; for 3h; Stage #2: With ammonia In methanol; water at 20 - 25℃; for 3h; Stage #3: With hydrogenchloride; pyrographite In ethanol at 55 - 60℃; for 1h; Temperature; Solvent;	92%

2-hydroxymethyl-3-cyano-4-hydroxy-n-butyraldehyde + methyl 2-aminopropanoate monohydrochloride (13515-97-4) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 2-hydroxymethyl-3-cyano-4-hydroxy-n-butyraldehyde; methyl 2-aminopropanoate monohydrochloride With sodium methylate In methanol at 30 - 50℃; for 5h; Green chemistry; Stage #2: With hydrogenchloride In methanol; water for 2h; Temperature; Solvent; Reagent/catalyst; Reflux; Green chemistry;	90.5%

4-methyl-5-dimethyl-tert-butylsiloxyoxazole + 2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 4-methyl-5-dimethyl-tert-butylsiloxyoxazole; 2-propyl-4,7-dihydro-2H-1,3-dioxepine at 115 - 120℃; for 10h; Stage #2: With water In ethanol at 20℃; for 3h; Stage #3: With hydrogenchloride In ethanol; water at 20℃; for 2h;	89.5%

Diels-Alder adduct (5205-63-0) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: Diels-Alder adduct With hydrogenchloride In ethanol; water at 20℃; for 2h; Stage #2: In ethanol; water for 2h;	86.05%

C8H13NO4 → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride; pyrographite In ethanol; water at 75 - 78℃; for 3h; Temperature;	83.5%

4-methyl-5-triisopropylsiloxyoxazole + 2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 4-methyl-5-triisopropylsiloxyoxazole; 2-propyl-4,7-dihydro-2H-1,3-dioxepine at 115 - 120℃; for 10h; Stage #2: With water In ethanol at 20℃; for 3h; Stage #3: With hydrogenchloride In ethanol; water at 20℃; for 2h;	82.7%

2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) + 4-methyl-5-butoxy1,3-oxazole (24201-52-3) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 2-propyl-4,7-dihydro-2H-1,3-dioxepine; 4-methyl-5-butoxy1,3-oxazole With calcium oxide at 150℃; for 12h; Diels-Alder Cycloaddition; Stage #2: With hydrogenchloride In ethanol; water at 20 - 60℃; for 12h; Stage #3: With hydrogenchloride In water for 1h; pH=8; Reagent/catalyst; Reflux;	80%

5-ethoxy-4-methyl-oxazole (5006-20-2) + 2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride Diels-Alder Cycloaddition;	78.5%

3-amino-4,5-bis(aminomethyl)2-methylpyridine trihydrochloride (90330-16-8) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 90℃; for 2h;	75%

2-Methyl-3-hydroxy-4,5-bis-(bromomethyl)-pyridine hydrobromide (39984-49-1) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With water; silver(I) chloride for 0.333333h; Heating;	68%
Multi-step reaction with 2 steps 1: 2.) AcONa / 1.) DMF, 55 degC, 1 h; 2.) DMF, 85 degC, 2.5 h 2: 98 percent / 2N HCl / H2O / 2 h / Heating View Scheme

pyridoxamine dihydrochloride (524-36-7) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With sulfuric acid; water; sodium nitrite at 20 - 90℃; for 2h;	25%

Thiamine hydrochloride (67-03-8) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With N-Bs In isopropyl alcohol at 25℃; for 0.5h;

L-1-Deoxy<1,1,1-(2)H3,(RS)-5-(2)H1>xylulose (80095-36-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With D-glucose; Escherichia coli B WG2 Mechanism;

3-amino-4-aminomethyl-5-hydroxymethyl-2-methylpyridine dihydrochloride (83537-53-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With cis-nitrous acid In water at 90℃;

Acetic acid 4-acetoxymethyl-2,5-dimethoxy-2-(1-methoxycarbonylamino-ethyl)-2,5-dihydro-furan-3-ylmethyl ester → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride In water Yield given;

hydrogenchloride (7647-01-0) + 4,5-bis-aminomethyl-2-methyl-pyridin-3-ol (45996-87-0) + aqueous NaNO2 → pyridoxal hydrochloride (58-56-0) + <5-chloromethyl>-3-hydroxy-2-methyl-<4>pyridyl>-methanol

hydrogenchloride (7647-01-0) + 4-ethoxymethyl-5-hydroxymethyl-2-methyl-pyridin-3-ol; hydrochloride → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
at 155 - 160℃;

5-amino-6-methylpyridine-3,4-dicarbonitrile (71058-42-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / conc. HCl, H2 / 5 percent Pd-C / methanol; H2O / 3.5 h / Ambient temperature 2: 75 percent / sodium nitrite, H2SO4 / H2O / 2 h / 90 °C View Scheme

5-acetoxymethyl-3-amino-2-methylpyridine-4-carbonitrile (83537-57-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / 1) conc. HCl, H2; 2) 0.2 N HCl / 1) 5 percent Pd-C / methanol; H2O / 1) 1 h, RT; 2) 1 h, 80 deg C 2: nitrous acid / H2O / 90 °C View Scheme

3,4-bis(hydroxymethyl)furan (14496-24-3) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / pyridine 2: 57 percent / p-toluenesulfonic acid / 2 h / 0 - 5 °C 3: electrochemical oxidation 4: HCl / H2O View Scheme

3,4-furan dimethanol diacetate (30614-73-4) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 57 percent / p-toluenesulfonic acid / 2 h / 0 - 5 °C 2: electrochemical oxidation 3: HCl / H2O View Scheme

Acetic acid 4-acetoxymethyl-2-(1-methoxycarbonylamino-ethyl)-furan-3-ylmethyl ester (79588-15-1) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: electrochemical oxidation 2: HCl / H2O View Scheme

1,3-dihydro-6-methyl-7-iodofuro(3,4-c)pyridine (104307-94-0) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 36 percent / Na, MeOH / CuI2 / various solvent(s) / 16 h / Heating 2: 78 percent / 48percent HBr / 2 h / Heating 3: 68 percent / H2O, AgCl / 0.33 h / Heating View Scheme

1,3-dihydro-6-methyl-7-methoxyfuro(3,4-c)pyridine (104307-95-1) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / 48percent HBr / 2 h / Heating 2: 68 percent / H2O, AgCl / 0.33 h / Heating View Scheme

1,3-dihydro-6-methyl-7-trimethylstannylfuro(3,4-c)pyridine (104307-93-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / I2 / CHCl3 / 18 h / Ambient temperature 2: 36 percent / Na, MeOH / CuI2 / various solvent(s) / 16 h / Heating 3: 78 percent / 48percent HBr / 2 h / Heating 4: 68 percent / H2O, AgCl / 0.33 h / Heating View Scheme

4,5'-O-isobutylidenepyridoxine (1622-67-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride; water under 300.03 Torr; for 2h; Product distribution / selectivity; Heating / reflux;
Stage #1: 4,5'-O-isobutylidenepyridoxine With hydrogenchloride; water In tetrahydrofuran at 60 - 120℃; under 150.015 Torr; for 3h; Stage #2: With pyrographite In water at 0 - 60℃; Product distribution / selectivity;

3-isopropyl-1,5-dihydro[1,3]dioxepino-3-methyl-4-n-butoxy-7-oxa-2-azabicyclo[2.2.1]hept-2-ene (717916-87-5) → pyridoxal hydrochloride (58-56-0) + 4,5'-O-isobutylidenepyridoxine (1622-67-9)

Conditions	Yield
Stage #1: 3-isopropyl-1,5-dihydro[1,3]dioxepino-3-methyl-4-n-butoxy-7-oxa-2-azabicyclo[2.2.1]hept-2-ene With water; acetic acid In tetrahydrofuran at 60℃; under 760.051 Torr; for 4h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 60℃; for 5h; Product distribution / selectivity;
Stage #1: 3-isopropyl-1,5-dihydro[1,3]dioxepino-3-methyl-4-n-butoxy-7-oxa-2-azabicyclo[2.2.1]hept-2-ene With water In tetrahydrofuran at 60℃; under 760.051 Torr; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran at 20 - 60℃; for 5h; Product distribution / selectivity;

concentrated H2 SO4 + pyridoxal hydrochloride (58-56-0) → isopropylidene pyridoxine

Conditions	Yield
In acetone	100%

pyridoxal hydrochloride (58-56-0) → 4,5-bis(chloromethyl)-3-hydroxy-2-methylpyridinium chloride (39984-50-4)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 0.5h; Reflux; Inert atmosphere;	99%
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 12h; Reflux;	96%
With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 3h;	93%

pyridoxal hydrochloride (58-56-0) + 4-aminobenzene sulfonic acid (121-57-3) → C14H14N2O5S (1122445-21-9)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With RuCl2(PPh3)2(BAOBEA); dihydrogen peroxide In water at 60℃; for 0.25h; Stage #2: 4-aminobenzene sulfonic acid In water for 0.0833333h; Reflux;	98.25%

pyridoxal hydrochloride (58-56-0) + 2,2-dimethoxy-propane (77-76-9) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol (1136-52-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃;	98%
With toluene-4-sulfonic acid In acetone at 20℃; for 23h;	96%
With toluene-4-sulfonic acid In acetone at 20℃; for 23h;	96%
With toluene-4-sulfonic acid In acetone at 20℃; for 20h; Inert atmosphere;	86%
With toluene-4-sulfonic acid In water; acetone for 20h; Inert atmosphere;	80%

pyridoxal hydrochloride (58-56-0) + acetic anhydride (108-24-7) → pyridoxine triacetate (10030-93-0)

Conditions	Yield
With triethylamine In tert-butyl methyl ether at 50 - 65℃; for 2.5h; Industry scale; Heating / reflux;	96%
With pyridine Ambient temperature;	57%
With pyridine

pyridoxal hydrochloride (58-56-0) + acetic anhydride (108-24-7) → 2,4-dimethyl-5-acetoxymethylpyridin-3-ol (53580-75-9)

Conditions	Yield
With zinc for 2h; Reflux;	95%

cobalt(II) chloride hexahydrate + Glutamic acid (617-65-2) + pyridoxal hydrochloride (58-56-0) → Co(2+)*C5HN(CH3)(O)(CH2OH)2(1-)*OOCCH2CH2(NH2)CHCOO(2-)*H(1+)*3H2O=Co{C5HN(CH3)(O)(CH2OH)2}(C5H8NO4)*3H2O

Conditions	Yield
With lithium carbonate In water byproducts: CO2; to soln. pyridoxine/water was added equimolar amt. glutamic acid and excess Li2CO3, after evolution CO2 completed addn. equimolar soln. CoCl2/H2O, formation of pink ppt.; ppt. separated, washed (EtOH and ether) until powdery, elem. anal.;	94.4%

pyridoxal hydrochloride (58-56-0) → 3-hydroxy-5-hydroxymethyl-2,4-dimethylpyridinium chloride (148-51-6)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With acetic acid; zinc for 12h; Reflux; Stage #2: With hydrogenchloride In methanol at 0℃; for 2h;	94%
Stage #1: pyridoxal hydrochloride With acetic acid; zinc for 12h; Reflux; Stage #2: With hydrogenchloride In methanol; water at 0℃; for 2h;	94%
With acetic acid; zinc for 24h; Reflux;	94%
Stage #1: pyridoxal hydrochloride With acetic acid; zinc at 120℃; for 3h; Stage #2: With hydrogenchloride In methanol at 60℃; for 1h;	93%
Multi-step reaction with 2 steps 1: zinc / 72 h / Reflux 2: hydrogenchloride / water / 8 h / 50 °C View Scheme

pyridoxal hydrochloride (58-56-0) → 4,5-bis-chloromethyl-2-methyl-pyridin-3-ol (102694-13-3)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 0.5h; Reflux;	93%
With thionyl chloride In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Reflux;	93%

pyridoxal hydrochloride (58-56-0) + 2,2-dimethoxy-propane (77-76-9) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol (1136-52-3) + 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5)

Conditions	Yield
With sulfuric acid In dichloromethane for 6h; Heating;	A 92% B n/a

pyridoxal hydrochloride (58-56-0) → 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With sulfuric acid In dichloromethane for 6h; Heating; Title compound not separated from byproducts;	A n/a B 92%

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol hydrochloride (6953-28-2)

Conditions	Yield
With hydrogenchloride	92%
With hydrogenchloride for 2.5h;	90.9%
With hydrogenchloride at 20 - 30℃; for 6h;	85%
With hydrogenchloride HCl introduction below 10 degC, then -10 degC, overnight;	54%
With hydrogenchloride at 0℃; for 2h;	27.3 g

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol (1136-52-3)

Conditions	Yield
With thionyl chloride In chloroform at 20℃; for 6h; ketalization;	91%
With sulfuric acid at 20℃;	65%
With Dess-Martin periodane; toluene-4-sulfonic acid at 20℃; for 20h; Inert atmosphere;	63%

pyridoxal hydrochloride (58-56-0) + cyclohexanone (108-94-1) → 3,4'-O-cyclohexylidenepyridoxine (4632-05-7)

Conditions	Yield
With thionyl chloride In chloroform at 20℃; ketalization;	90%
With sulfuric acid
Acidic conditions;

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5)

Conditions	Yield
With thionyl chloride In chloroform at 0 - 20℃; for 7h; ketalization;	90%
With hydrogenchloride at 3 - 20℃;	87%
(i) HCl, (ii) aq. K2CO3; Multistep reaction;

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → chlorhydrate d'hydroxy-8 trimethyl-2,2,7 pyrido-<4,5-e>dioxa 1,3-cycloheptane (111422-99-2)

Conditions	Yield
With hydrogenchloride at 0℃; for 1h;	88%

Decan-2-one (693-54-9) + pyridoxal hydrochloride (58-56-0) → 5-(hydroxymethyl)-2,8-dimethyl-2-octyl-4H-[1,3]dioxino[4,5-c]pyridine

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 17h; Reflux; Dean-Stark;	87%

pyridoxal hydrochloride (58-56-0) + benzoic acid hydrazide (613-94-5) → N'-{(3-hydroxyl-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene}benzohydrazide hydrochloride

Conditions	Yield
Stage #1: pyridoxal hydrochloride With manganese(IV) oxide; sulfuric acid In water at 60 - 70℃; Stage #2: benzoic acid hydrazide In water for 0.166667h; Heating;	86%

4,4'-dimethoxytrityl chloride (40615-36-9) + pyridoxal hydrochloride (58-56-0) → C50H47NO7

Conditions	Yield
In pyridine; dichloromethane at 20℃; Inert atmosphere;	85%

pyridoxal hydrochloride (58-56-0) + tert-butylchlorodiphenylsilane (58479-61-1) → C40H47NO3Si2

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	83%
With triethylamine In tetrahydrofuran for 1.5h; Cooling with ice;	67%

pyridoxal hydrochloride (58-56-0) + benzyl bromide (100-39-0) → [5-(benzyloxy)-4-(hydroxymethyl)-6-methylpyridin-3-yl]methanol (7442-21-9)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With potassium carbonate In acetonitrile at 90℃; for 1h; Stage #2: benzyl bromide In acetonitrile for 3h; Reflux;	83%

Upstream product

• 5006-20-2 5-Ethoxy-4-methyloxazole 
• 108-21-4 Isopropyl acetate 

Downstream Products

• 65-22-5 Pyridoxal hydrochloride 
• 82-82-6 4-PYRIDOXIC ACID 
• 524-36-7 Pyridoxamine dihydrochloride 

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