93-17-4

Basic information

• Product Name: (3,4-Dimethoxyphenyl)acetonitrile
• Synonyms: 3,4-Dimethoxylphenylacetonitrile;(3,4-Dimethoxyphenyl)acetonitrile, 3,4-Dimethoxybenzylcyanide, Homoveratronitrile;(3,4-Dimethoxyphenyl)acetonitrile, 3,4-Dimethoxybenzylcyanide;1-Cyanomethyl-3,4-dimethoxybenzene;(3,4-Dimethoxyphenyl;4-DiMethyloxy phenylacetonotrile;(3,4-DiMethoxyphenyl)acetonitrile, 99+% 25GR;NSC 6324
• CAS NO: 93-17-4
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 202-225-1
• Product Categories: Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Catechol Derivatives;Aromatic Nitriles;Nitriles
• Mol File: 93-17-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 54-57 °C(lit.)
• Boiling Point: 171-178 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: yellow/Crystals or Crystalline Needles
• Density: 1.1607 (rough estimate)
• Vapor Pressure: 0.000333mmHg at 25°C
• Refractive Index: 1.5168 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: methanol: 0.1 g/mL, clear
• Water Solubility: insoluble
• BRN: 1956100
• CAS DataBase Reference: (3,4-Dimethoxyphenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3,4-Dimethoxyphenyl)acetonitrile(93-17-4)
• EPA Substance Registry System: (3,4-Dimethoxyphenyl)acetonitrile(93-17-4)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-23/24/25-36/37/38-20/21/22
• Safety Statements: 36/37-45-22-36-26
• RIDADR: 3276
• WGK Germany: 3
• RTECS: AL9325000
• HazardClass: IRRITANT
• Hazardous Substances Data: 93-17-4(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white crystals or cryst. needles

Uses

Different sources of media describe the Uses of 93-17-4 differently. You can refer to the following data:
1. An Impurity of Verapamil (V125000). An intermediate in the preparation of the muscle relaxant Papverine (P190500).
2. (3,4-Dimethoxyphenyl)acetonitrile has been used in the synthesis of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile. It has also been used in the preparation of modified diterpene (±) nimbidiol which relies on a sulfenium ion promoted polyene cyclization.

Synthesis Reference(s)

Journal of the American Chemical Society, 57, p. 1126, 1935 DOI: 10.1021/ja01309a053Tetrahedron Letters, 24, p. 4533, 1983 DOI: 10.1016/S0040-4039(00)85947-X

Purification Methods

Its solubility is 10% in MeOH, and it has been recrystallised from EtOH or MeOH. Purify it also by distillation followed by recrystallisation. [Price & Rogers Org Synth Coll Vol III 174 1955, Niederl & Ziering J Am Chem Soc 64 885 1952, Julian & Sturgis J Am Chem Soc 57 1126 1935, Beilstein 10 I 198.]

InChI:InChI=1/C10H11NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5H2,1-2H3

Synthetic route

2-(3,4-dimethoxyphenyl)acetamide (5663-56-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With ethyl phosphodichloridite; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h;	92%

4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With sodium cyanide	91%

α-(3,4-dimethoxyphenyl)-α-(methylthio)acetonitrile (84784-38-3) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With acetic acid; zinc at 100℃; for 1h;	90%

2-(3,4-dimethoxyphenyl)acetaldehyde oxime (77733-60-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With trimethylsilyl iodide; 1,1,1,3,3,3-hexamethyl-disilazane In chloroform at 56℃; for 4h;	86%
With trimethylsilyl iodide; 1,1,1,3,3,3-hexamethyl-disilazane In chloroform at 56℃; for 4h; Product distribution; other temperature, without hexamethyldisilazane (TMS2NH);	86%
With acetic anhydride
With trimethylsilyl iodide In chloroform for 2h; Ambient temperature;	40 mg

4-isoxazoleboronic acid pinacol ester (928664-98-6) + 4-Bromoveratrole (2859-78-1) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water In dimethyl sulfoxide at 130℃; for 16h; Domino Suzuki coupling and fragmentation reaction; Inert atmosphere;	84%

3,4-Dimethoxyphenylthioacetamid (145736-65-8) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With 1-oxa-2-azaspiro[2.5]octane In toluene at 20 - 25℃; for 4h;	82%

4-Bromoveratrole (2859-78-1) + acetonitrile (75-05-8) → 3,4-dimethoxyphenylacetonitrile (93-17-4) + bis(3,4-dimethoxyphenyl)acetonitrile (7250-04-6)

Conditions	Yield
With ethoxyethoxyethanol; sodium amide In 1,2-dimethoxyethane 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -45 deg C, 4.5 h;	A 78% B 8%

sodium cyanide (143-33-9) + 1-(3,4-Dimethoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide (76950-82-8) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
In 1,2-dimethoxyethane for 24h; Heating;	76%

potassium cyanide (151-50-8) + 4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
In dimethyl sulfoxide for 20h;	67%
With benzene
With hydrogenchloride

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 65℃; for 3h;	64%

2-bromo-4,5-dimethoxyphenylacetonitrile (51655-39-1) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
Stage #1: 2-bromo-4,5-dimethoxyphenylacetonitrile With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran for 0.25h; Schlenk technique; Glovebox; Stage #2: In tetrahydrofuran at 35℃; for 72h; Irradiation;	54%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) + 4-(methylsulfonyl)benzonitrile (22821-76-7) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With riboflavin-2',3',4',5'-tetra-acetate In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation; Sealed tube;	45%

3,4-dimethoxyphenylpyruvic acid (2460-33-5) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With acetic anhydride

2-(3,4-dimethoxyphenyl)acetaldehyde oxime (77733-60-9) + acetic anhydride (108-24-7) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

3,4-dimethoxy-α-ethoxycarbonyloxybenzyl cyanide (6443-67-0) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With p-menth-1-ene; palladium on activated charcoal

sodium cyanide (143-33-9) + (3,4-dimethoxyphenyl)methanol (93-03-8) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
(i) aq. HCl, CH2Cl2, (ii) /BRN= 3587243/, KI, acetone; Multistep reaction;
(i) aq. HCl, (ii) /BRN= 3587243/, DMSO; Multistep reaction;

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + sodium cyanide (143-33-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
In ethanol; water for 5h; Heating;

ethyl 2-cyano-2-(3,4-dimethoxyphenyl)acetate (36848-69-8) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With sodium hydroxide In water at 80 - 90℃; for 2h; Yield given;

Phosphoric acid cyano-(3,4-dimethoxy-phenyl)-methyl ester diethyl ester (96824-26-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 2h; Ambient temperature; Yield given;

3-hydroxy-4-methoxyphenylacetonitrile (4468-58-0) + dimethyl sulfate (77-78-1) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With sodium hydroxide at 0℃; for 1h;

sodium cyanide (143-33-9) + 4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
In 1,4-dioxane; water
In water; benzene for 6h; Heating; Yield given;

sodium cyanide (143-33-9) + 4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4) + (Z)-1,2-dicyano-1,2-bis(3,4-dimethoxyphenyl)ethene (18656-85-4)

Conditions	Yield
In tetrachloromethane; water Heating;

(+-)-benzoyloxy-<3.4-dimethoxy-phenyl>-acetonitrile → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With p-menth-1-ene; palladium
With tetralin; palladium

3.4-dimethoxy-phenylpyruvic acid-oxime → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
at 155℃;

ethoxycarbonyloxy-<3,4-dimethoxy-phenyl>-acetonitrile → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With palladium; benzene Hydrogenation;

oxime of homoveratraldehyde → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
With acetic anhydride

tetralin (119-64-2) + 2-benzoyloxy-2-(3',4'-dimethoxyphenyl)-acetonitrile (102327-45-7) + palladium → 3,4-dimethoxyphenylacetonitrile (93-17-4)

2-benzoyloxy-2-(3',4'-dimethoxyphenyl)-acetonitrile (102327-45-7) + (R)-p-menthene-(1) + palladium → 3,4-dimethoxyphenylacetonitrile (93-17-4)

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + potassium cyanide (151-50-8) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Conditions	Yield
In ethanol; water for 4h; Substitution; Heating;

3,4-dimethoxyphenylacetonitrile (93-17-4) → 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid for 4h;	100%
Stage #1: 3,4-dimethoxyphenylacetonitrile With diborane In tetrahydrofuran at 55℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; Stage #3: With sodium hydroxide In tetrahydrofuran; water	99%
With hydrogen; nickel In ethanol at 40℃; electrocatalytic hydrogenation;	98%

3,4-dimethoxyphenylacetonitrile (93-17-4) → homoveratrylamine hydrochloride (635-85-8)

Conditions	Yield
With hydrogenchloride; hydrogen In propan-1-ol; water at 60℃; under 375.038 Torr; for 18h; Flow reactor;	100%
Stage #1: 3,4-dimethoxyphenylacetonitrile With borane-ammonia complex; C17H16BrMnN2O3S In hexane at 60℃; for 12h; Stage #2: With hydrogenchloride In diethyl ether; water	90%

1-η**(5)-ferrocenyl-3,3-bis(methylthio)prop-2-en-1-one (916322-38-8) + 3,4-dimethoxyphenylacetonitrile (93-17-4) → C24H23FeNO3S

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil; benzene at 0℃; for 0.25h; Stage #2: 3,3-bis(methylsulfanyl)-1-η5-ferrocenyl-2-propen-1-one In N,N-dimethyl-formamide; mineral oil; benzene at 0 - 20℃;	100%

3,4-dimethoxyphenylacetonitrile (93-17-4) + 4-methoxy-benzaldehyde (123-11-5) → (Z)-2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile (37629-77-9)

Conditions	Yield
With sodium ethanolate In ethanol Reflux; Inert atmosphere;	99%
With sodium methylate In ethanol at 20℃; for 3h;	92%
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;	90%

ethanol (64-17-5) + 3,4-dimethoxyphenylacetonitrile (93-17-4) → ethyl 2-(3,4-dimethoxyphenyl)acetoimidate hydrochloride (81316-62-3)

Conditions	Yield
With hydrogenchloride at 0 - 5℃; Addition;	99%
With hydrogenchloride	88%
With hydrogenchloride In chloroform for 2h; Ambient temperature;
With hydrogenchloride In diethyl ether

3,4-dimethoxyphenylacetonitrile (93-17-4) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (Z)-α-(3,4-dimethoxyphenyl)-3,4-dimethoxycinnamonitrile (37629-72-4)

Conditions	Yield
With sodium ethanolate In ethanol at 85℃; for 1h;	98%
With sodium ethanolate In ethanol for 1h; Reflux; Inert atmosphere;	97%
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;	97%

3,4-dimethoxyphenylacetonitrile (93-17-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → Z-2-(3,4-dimethoxyphenyl)-3-dimethylaminoacrylonitrile

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Reflux;	98%

3,4-dimethoxyphenylacetonitrile (93-17-4) → 2-(3,4-dimethoxyphenyl)ethan-1,1-d2-1-amine hydrochloride

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetonitrile With samarium diiodide; water-d2; triethylamine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride In water regioselective reaction;	98%
Stage #1: 3,4-dimethoxyphenylacetonitrile With samarium diiodide; water-d2; triethylamine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride	98%
Stage #1: 3,4-dimethoxyphenylacetonitrile With ethyl [2]alcohol; sodium In hexane; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether	92%

4-[(6-hydroxyhexyl)oxy]-3,5-dimethoxybenzaldehyde (154786-34-2) + 3,4-dimethoxyphenylacetonitrile (93-17-4) → (2Z)-2-(3,4-dimethoxyphenyl)-3-{4-[(6-hydroxyhexyl)oxy]-3,5-dimethoxyphenyl}prop-2-enenitrile (1425539-63-4)

Conditions	Yield
	97%

Pentafluorobenzene (363-72-4) + 3,4-dimethoxyphenylacetonitrile (93-17-4) → α-(3',4'-Dimethoxyphenyl)-2,3,5,6-tetrafluorophenylacetonitrile

Conditions	Yield
With lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; regioselective reaction;	97%

3,4-dimethoxyphenylacetonitrile (93-17-4) + hexan-1-ol (111-27-3) → α-<3.4-Dimethoxy-phenyl>-caprylsaeurenitril (93148-41-5)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;	97%

3,4-dimethoxyphenylacetonitrile (93-17-4) + O,N-bisbenzenesulfonyl-N-methylethanolamine (85753-64-6) → N-[3-Cyano-3-(3,4-dimethoxy-phenyl)-propyl]-N-methyl-benzenesulfonamide (85753-65-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran for 1.5h; -78 deg C -> 25 deg C;	96%
With n-butyllithium 1.) THF, -25 deg C; Yield given. Multistep reaction;

3,4-dimethoxyphenylacetonitrile (93-17-4) → 2-(2-iodo-4,5-dimethoxyphenyl)acetonitrile (58432-84-1)

Conditions	Yield
With iodine; silver trifluoroacetate In dichloromethane at -10 - -5℃;	96%
With iodine; silver trifluoroacetate In dichloromethane at -5℃; for 0.1h;	93%
With Iodine monochloride; acetic acid at 20℃;	72%

3,4-dimethoxyphenylacetonitrile (93-17-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,4-dimethoxy-N,N-dimethylbenzothioamide

Conditions	Yield
With sulfur; copper acetylacetonate; potassium carbonate at 110℃; for 24h; Schlenk technique;	96%

3,4-dimethoxyphenylacetonitrile (93-17-4) + 3-ethoxy-4-[(6-hydroxyhexyl)oxy]benzaldehyde (1425539-56-5) → (2Z)-2-(3,4-dimethoxyphenyl)-3-{3-ethoxy-4-[(6-hydroxyhexyl)oxy]phenyl}prop-2-enenitrile (1425539-57-6)

Conditions	Yield
	96%

3,4-dimethoxyphenylacetonitrile (93-17-4) + dimethyl amine (124-40-3) → 2-(3,4-dimethoxyphenyl)-N,N-dimethylacetamidine

Conditions	Yield
With copper(l) chloride In ethanol; water at 20 - 70℃; for 24h; Inert atmosphere;	96%

3,4-dimethoxyphenylacetonitrile (93-17-4) + Diethyl carbonate (105-58-8) → ethyl 2-cyano-2-(3,4-dimethoxyphenyl)acetate (36848-69-8)

Conditions	Yield
Stage #1: With ethanol; sodium In toluene at 80 - 85℃; for 2h; Stage #2: 3,4-dimethoxyphenylacetonitrile; Diethyl carbonate In toluene at 80℃; for 2h;	95.6%
With sodium at 110℃; for 1h;	80%
Stage #1: 3,4-dimethoxyphenylacetonitrile With sodium In ethanol; toluene Stage #2: Diethyl carbonate at 80℃;

3,4-dimethoxyphenylacetonitrile (93-17-4) → 2-bromo-4,5-dimethoxyphenylacetonitrile (51655-39-1)

Conditions	Yield
With N-Bromosuccinimide; trifluoroacetic acid In acetonitrile at 20℃; for 6h;	95%
With bromine; sodium acetate; acetic acid
With N-Bromosuccinimide; trifluoroacetic acid In acetonitrile at 20℃; for 16h;	15.3 g

3,4-dimethoxyphenylacetonitrile (93-17-4) + cyclohexanone (108-94-1) → 1-[cyano-(3,4-dimethoxyphenyl)-methyl]cyclohexanol

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 0 - 15℃; for 1h;	95%
With sodium hydroxide; benzyltrimethylammonium chloride In water at 0 - 15℃;	71%

2-Aminonicotinaldehyde (7521-41-7) + 3,4-dimethoxyphenylacetonitrile (93-17-4) → 3-(3,4-dimethoxyphenyl)-[1,8]naphthyridin-2-ylamine (1075240-57-1)

Conditions	Yield
With aminosulfonic acid for 0.05h; microwave irradiation;	95%

3,4-dimethoxyphenylacetonitrile (93-17-4) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → (Z)-3-(3,4,5-trimethoxyphenyl)-2-(3,4-dimethoxyphenyl)acrylonitrile

Conditions	Yield
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;	95%

3,4-dimethoxyphenylacetonitrile (93-17-4) → 5-(3',4'-dimethoxybenzyl)-1H-tetrazole

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide for 24h; Reflux;	95%

3,4-dimethoxyphenylacetonitrile (93-17-4) → C10H9(2)H2NO2

Conditions	Yield
With water-d2; triethylamine at 20℃; for 24h; Inert atmosphere;	95%

3,4-dimethoxyphenylacetonitrile (93-17-4) → 2-(3,4-dimethoxyphenyl)acetamide (5663-56-9)

Conditions	Yield
With potassium hydroxide In tert-butyl alcohol for 1h; Reagent/catalyst; Solvent; Reflux;	94%
With hydrogenchloride
Multi-step reaction with 3 steps 1: aq.-ethanolic KOH-solution 2: hydrogen chloride 3: aqueous ammonia View Scheme
With Rhodococcus rhodochrous ATCC BAA 870 cobalt nitrile hydratase In aq. buffer at 30℃; pH=7.6; Enzymatic reaction;

3,4-dimethoxyphenylacetonitrile (93-17-4) + 4-chlorobenzaldehyde (104-88-1) → (Z)-3-(4-chlorophenyl)-2-(3,4-dimethoxyphenyl)acrylonitrile (37629-70-2)

Conditions	Yield
With sodium methylate In ethanol at 20℃; for 2h;	94%
With ethanol; sodium ethanolate

3,4-dimethoxyphenylacetonitrile (93-17-4) + benzaldehyde (100-52-7) → (Z)-2-(3,4-dimethoxyphenyl)-3-phenylacrylonitrile (2958-55-6)

Conditions	Yield
With sodium methylate In ethanol at 20℃; for 2h;	94%
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel condensation; Inert atmosphere;	77%
With ethanol; sodium ethanolate
With sodium ethanolate In ethanol Heating;

3,4-dimethoxyphenylacetonitrile (93-17-4) + 2-azidobenzaldehyde (16714-25-3) → 4-(3,4-Dimethoxy-phenyl)-1,2,3,9b-tetraaza-cyclopenta[a]naphthalene

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile for 12h; Ambient temperature;	94%

3,4-dimethoxyphenylacetonitrile (93-17-4) + methyl iodide (74-88-4) → 2‐(3,4‐dimethoxyphenyl)‐2‐methylpropionitrile (23023-16-7)

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran for 12h; Product distribution / selectivity;	94%
Stage #1: 3,4-dimethoxyphenylacetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;	93%
Stage #1: 3,4-dimethoxyphenylacetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;	93%

3,4-dimethoxyphenylacetonitrile (93-17-4) + 2,3,4-trimethoxybenzaldehyde (2103-57-3) → (Z)-3-(2,3,4-trimethoxyphenyl)-2-(3,4-dimethoxyphenyl)acrylonitrile (1151666-74-8)

Conditions	Yield
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;	94%
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;	94%

N-Acetylimidazole (2466-76-4) + 3,4-dimethoxyphenylacetonitrile (93-17-4) → α-(3,4-dimethoxyphenyl)acetoacetonitrile (18133-46-5, 63895-79-4)

Conditions	Yield
With lithium hydride In dimethyl sulfoxide at 20℃; for 0.5h;	94%

Upstream product

• 77733-60-9 2-(3,4-dimethoxyphenyl)acetaldehyde oxime 
• 108-24-7 acetic anhydride 
• 151-50-8 potassium cyanide 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 6443-67-0 3,4-dimethoxy-α-ethoxycarbonyloxybenzyl cyanide 
• 36848-69-8 ethyl 2-cyano-2-(3,4-dimethoxyphenyl)acetate 
• 145736-65-8 3,4-Dimethoxyphenylthioacetamid 
• 119-64-2 tetralin 
• 102327-45-7 2-benzoyloxy-2-(3',4'-dimethoxyphenyl)-acetonitrile 
• 13435-20-6 tetraethylammoniumcyanide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 2859-78-1 4-Bromoveratrole 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 101097-43-2 2-(3,4-dimethoxy-phenyl)-3c-[2]furyl-acrylonitrile 
• 106737-74-0 2-(3,4-dimethoxy-phenyl)-3c-[2]thienyl-acrylonitrile 
• 109805-22-3 3c-[4]quinolyl-2-(3,4-dimethoxy-phenyl)-acrylonitrile 
• 102006-98-4 2-(3,4-dimethoxy-phenyl)-3c-[3]isoquinolyl-acrylonitrile 
• 83459-58-9 2,4,6,3',4'-pentamethoxy-deoxybenzoin 
• 53084-06-3 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)-ethanone 
• 109694-40-8 (6,7-dimethoxy-cinnolin-4-yl)-(3,4-dimethoxy-phenyl)-acetonitrile 
• 709025-88-7 2-(3,4-dimethoxy-phenyl)-3-oxo-5-phenyl-valeronitrile 
• 859967-82-1 4-benzyloxy-2-(3,4-dimethoxy-phenyl)-acetoacetonitrile 
• 66116-74-3 1-(2,4,5-trihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone 
• 859967-81-0 2-(3,4-dimethoxy-phenyl)-4-phenoxy-acetoacetonitrile 
• 857816-53-6 2-(3,4-dimethoxy-phenyl)-4-(N-methyl-anilino)-acetoacetonitrile 
• 857808-38-9 2,5-bis-(3,4-dimethoxy-phenyl)-4-methyl-3-oxo-valeric acid amide 
• 857816-57-0 4-(2,3-dimethoxy-phenoxy)-2-(3,4-dimethoxy-phenyl)-acetoacetonitrile 

Relevant articles and documents

Total synthesis of isopavine and intermediates for the preparation of substituted amitriptyline analogues: Facile routes to substituted dibenzocyclooctatrienes and dibenzocycloheptatrienes

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Nickel-Catalyzed Photodehalogenation of Aryl Bromides

Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible-light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts and is characterized by its simplicity and broad scope, including challenging substrate combinations.

Production technology of 3,4-dimethoxy phenethylamine

A production technology of 3,4-dimethoxyphenethylamine is disclosed, and characterized by using 3,4-dihydroxybenzyl chloride and dimethyl sulfate as raw materials; performing an etherification reaction to generate 3,4-dimethoxybenzyl chloride in the presence of sodium hydrate; performing an cyanation reaction on the 3,4-dimethoxybenzyl chloride and a cyanide compound to generate 3,4-dimethoxybenzyl cyanide; cooling the 3,4-dimethoxybenzyl cyanide in propanone for crystallization to obtain 3,4-dimethoxybenzyl cyanide crystals; subjecting 3,4-dimethoxybenzyl cyanide to catalytic ammoniation and hydrogenation in a solvent to generate 3,4-dimethoxyphenethylamine; and performing reduced-pressure distillation on the product obtained after ammoniation and hydrogenation to obtain an qualified product of 3,4-dimethoxyphenethylamine. The overall product yield is 86% or higher.