6470-18-4

Basic information

• Product Name: 1-Acetamido-7-hydroxynaphthalene
• Synonyms: ACETAMIDE, N-(7-HYDROXY-1-NAPHTHALENYL)-;1-ACETHYL AMINO-7 NAPTHTHOL;1-Acetamido-7-hydroxynaphthalene;1-acetamido-7-naphthol;1-ACETYLAMINO-7-NAPHTHOL;4'-Nitrophenyl-1-Hydroxy-2-Naphthionate;1-ACETAMINO-7-NAPHTHOL;1-Acetamino-7-hydroxynaphthalin
• CAS NO: 6470-18-4
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22
• EINECS: 229-293-5
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 6470-18-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 168-169 °C
• Boiling Point: 486.2 °C at 760 mmHg
• Flash Point: 247.9 °C
• Appearance: /
• Density: 1.297 g/cm³
• Vapor Pressure: 4.45E-10mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.44±0.40(Predicted)
• CAS DataBase Reference: 1-Acetamido-7-hydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetamido-7-hydroxynaphthalene(6470-18-4)
• EPA Substance Registry System: 1-Acetamido-7-hydroxynaphthalene(6470-18-4)

Safety Data

• Hazardous Substances Data: 6470-18-4(Hazardous Substances Data)

Usage

Uses

Intermediate of dyestuff

InChI:InChI=1/C12H11NO2/c1-8(14)13-12-4-2-3-9-5-6-10(15)7-11(9)12/h2-7,15H,1H3,(H,13,14)

Synthetic route

8-acetamidonaphthalen-2-yl acetate (29921-56-0) → 1-acetylamino-7-naphthol (6470-18-4)

Conditions	Yield
With sodium hydrogencarbonate In methanol for 1h; Reflux;	96%
With sodium hydrogencarbonate In methanol

8-amino-2-naphthol (118-46-7) + acetic anhydride (108-24-7) → 1-acetylamino-7-naphthol (6470-18-4)

Conditions	Yield
In dichloromethane at 20℃; for 21h;	88%

8-amino-2-naphthol (118-46-7) + acetyl chloride (75-36-5) → 8-acetamidonaphthalen-2-yl acetate (29921-56-0) + 1-acetylamino-7-naphthol (6470-18-4)

Conditions	Yield
With pyridine; benzene

8-amino-2-naphthol (118-46-7) → 1-acetylamino-7-naphthol (6470-18-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: TEA / CHCl3 2: NaHCO3 (sat) / methanol View Scheme
With acetic anhydride In methanol
In ice-water

8-amino-2-naphthalenesulfonic acid (119-28-8) → 1-acetylamino-7-naphthol (6470-18-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; water / 250 - 260 °C View Scheme

8-amino-2-naphthol (118-46-7) + acetic acid (64-19-7) → 1-acetylamino-7-naphthol (6470-18-4)

Conditions	Yield
With sodium hydroxide at 20 - 40℃; for 2h;	120 g

1-acetylamino-7-naphthol (6470-18-4) + methyl iodide (74-88-4) → N-(7-methoxynaphthalen-1-yl)acetamide (93189-18-5)

Conditions	Yield
With potassium carbonate In acetone for 1h; Reflux;	90%
With potassium carbonate In acetone for 6h; Heating;
With potassium carbonate In acetone

2-ethylhexyl bromide (18908-66-2) + 1-acetylamino-7-naphthol (6470-18-4) → C20H27NO2

Conditions	Yield
With potassium carbonate In acetonitrile for 9h; Reflux;	88%
With potassium carbonate In acetonitrile for 9h; Reflux;	88%

trifluoromethane anhydride + 1-acetylamino-7-naphthol (6470-18-4) → 2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene (168901-50-6)

Conditions	Yield
With dmap; trifluoromethanesulfonic acid anhydride In dichloromethane	69.5%

ethanolamine (141-43-5) + 1-acetylamino-7-naphthol (6470-18-4) → 9-acetylamino-2-hydroxymethyl naphtho[2,1-d]oxazole (1627144-25-5)

Conditions	Yield
With copper dichloride In acetonitrile at 60℃; for 15h;	62%

1-acetylamino-7-naphthol (6470-18-4) → N-(7,8-dioxo-7,8-dihydronaphthalen-1-yl)acetamide (950-84-5)

Conditions	Yield
With tert.-butylhydroperoxide; 3 A molecular sieve; titanium(IV) isopropylate In dichloromethane for 16h;	58%

acetic anhydride (108-24-7) + 1-acetylamino-7-naphthol (6470-18-4) → 8-acetamidonaphthalen-2-yl acetate (29921-56-0)

Conditions	Yield
With sodium acetate; acetic acid

acetic anhydride (108-24-7) + 1-acetylamino-7-naphthol (6470-18-4) → 7-acetoxy-1-diacetylamino-naphthalene

Conditions	Yield
With sodium acetate; acetic acid

dimethyl sulfate (77-78-1) + 1-acetylamino-7-naphthol (6470-18-4) → N-(7-methoxynaphthalen-1-yl)acetamide (93189-18-5)

Conditions	Yield
With sodium hydroxide

benzenediazonium (2684-02-8) + 1-acetylamino-7-naphthol (6470-18-4) → N-(7-hydroxy-8-phenylazo-[1]naphthyl)-acetamide

4-sulfobenzenediazonium (2154-66-7) + 1-acetylamino-7-naphthol (6470-18-4) → 4-(8-amino-2-hydroxy-[1]naphthylazo)-benzenesulfonic acid

Conditions	Yield
bei der Behandlung des Reaktionsgemisches mit warmer Natronlauge;

diazotierte 2-Amino-benzol-disulfonsaeure-(1.4) (122290-34-0) + 1-acetylamino-7-naphthol (6470-18-4) → 2-(8-acetylamino-2-hydroxy-[1]naphthylazo)-benzene-1,4-disulfonic acid

1-acetylamino-7-naphthol (6470-18-4) → 8-acetylamino-[1,2]naphthoquinone-1-oxime

Conditions	Yield
With sodium nitrite Ansaeuern mit verd. Schwefelsaeure;

C. I. disperse red 60 (17418-58-5) + 1-acetylamino-7-naphthol (6470-18-4) → N-[7-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-naphthalen-1-yl]-acetamide (38919-97-0)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium hydroxide at 145 - 150℃;

cis-nitrous acid (7782-77-6) + 1-acetylamino-7-naphthol (6470-18-4) → 8-acetylamino-[1,2]naphthoquinone-1-oxime

hydrogenchloride (7647-01-0) + iron(III) chloride (7705-08-0) + 1-acetylamino-7-naphthol (6470-18-4) → 8.8'-bis-acetylamino-2.2'-dioxo-2H.2'H-<1.1'>binaphthylidene

nitrobenzene (98-95-3) + 1-acetylamino-7-naphthol (6470-18-4) + copper (II)-oxide → 8.8'-bis-acetylamino-2.2'-dioxo-2H.2'H-<1.1'>binaphthylidene

1-acetylamino-7-naphthol (6470-18-4) + diazotized 4-amino-3-hydroxy-benzenesulfonic acid → 4-(8-acetylamino-2-hydroxy-[1]naphthylazo)-3-hydroxy-benzenesulfonic acid amide

Conditions	Yield
With sodium hydroxide; sodium carbonate

1-acetylamino-7-naphthol (6470-18-4) → N-(8-bromo-7-hydroxy-naphthalen-1-yl)-acetamide (871732-00-2)

Conditions	Yield
With bromine In acetic acid for 14h;

1-acetylamino-7-naphthol (6470-18-4) → 2-methylbenzo[cd]indol-3(1H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Br2 / acetic acid / 14 h 2.1: 4.54 g / imidazole / dimethylformamide / 1 h 3.1: MeLi / tetrahydrofuran; diethyl ether / 1 h / -78 °C 3.2: t-BuLi / tetrahydrofuran; diethyl ether; pentane / 2 h / -78 - 0 °C 3.3: 91 percent / NH4Cl / tetrahydrofuran; diethyl ether; various solvents View Scheme

1-acetylamino-7-naphthol (6470-18-4) → N-{8-bromo-7-[[tris(1-methylethyl)silyl]oxy]}acetamide (871731-86-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / acetic acid / 14 h 2: 4.54 g / imidazole / dimethylformamide / 1 h View Scheme

1-acetylamino-7-naphthol (6470-18-4) → 3,6-dibromo-8-chloro-2-naphthol (550998-29-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: K2CO3 / acetone / 6 h / Heating 2: aq. HCl / 5 h / Heating 3: tert-butyl nitrite; CuCl2 / acetonitrile / 0 - 20 °C 4: 92 percent / BBr3 / CH2Cl2 / 0 - 20 °C 5: Br2; acetic acid / 1 h / 100 °C View Scheme

1-acetylamino-7-naphthol (6470-18-4) → 1,6-dibromo-8-fluoro-2-naphthol (550998-28-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: K2CO3 / acetone / 6 h / Heating 2.1: aq. HCl / 5 h / Heating 3.1: aq. HCl; NaNO2 / 0.5 h / 10 °C 3.2: aq. HBF4 3.3: xylene / 1 h / Heating 4.1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 5.1: 62 percent / Br2; acetic acid / 1 h / 100 °C View Scheme

1-acetylamino-7-naphthol (6470-18-4) → 1,3,6-tribromo-8-chloro-naphthalen-2-ol

Conditions	Yield
Multi-step reaction with 5 steps 1: K2CO3 / acetone / 6 h / Heating 2: aq. HCl / 5 h / Heating 3: tert-butyl nitrite; CuCl2 / acetonitrile / 0 - 20 °C 4: 92 percent / BBr3 / CH2Cl2 / 0 - 20 °C 5: 1.80 g / Br2; acetic acid / 1 h / 100 °C View Scheme

1-acetylamino-7-naphthol (6470-18-4) → 8-chloro-6-(4-methoxyphenyl)-2-naphthol (550998-42-0)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: K2CO3 / acetone / 6 h / Heating 2.1: aq. HCl / 5 h / Heating 3.1: tert-butyl nitrite; CuCl2 / acetonitrile / 0 - 20 °C 4.1: 92 percent / BBr3 / CH2Cl2 / 0 - 20 °C 5.1: Br2; acetic acid / 1 h / 100 °C 6.1: 84 percent / imidazole / dimethylformamide / 3 h 7.1: 69 percent / Pd[P(Ph)3]4 / tetrahydrofuran / 3 h / Heating 8.1: 88 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 9.1: t-BuLi / tetrahydrofuran / 0.33 h / -78 °C 9.2: H2O / tetrahydrofuran / -78 - 20 °C View Scheme

1-acetylamino-7-naphthol (6470-18-4) → 8-fluoro-6-(4-methoxyphenyl)-2-naphthol (550998-32-8)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: K2CO3 / acetone / 6 h / Heating 2.1: aq. HCl / 5 h / Heating 3.1: aq. HCl; NaNO2 / 0.5 h / 10 °C 3.2: aq. HBF4 3.3: xylene / 1 h / Heating 4.1: 3.99 g / BBr3 / CH2Cl2 / 0 - 20 °C 5.1: 62 percent / Br2; acetic acid / 1 h / 100 °C 6.1: 41 percent / SnCl2; aq. HCl; acetic acid / 1 h / 100 °C 7.1: 81 percent / aq. Na2CO3; Pd[P(Ph)3]4 / 1,2-dimethoxy-ethane / 85 °C View Scheme

Upstream product

• 118-46-7 8-amino-2-naphthol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 
• 119-28-8 8-amino-2-naphthalenesulfonic acid 
• 29921-56-0 8-acetamidonaphthalen-2-yl acetate 

Downstream Products

• 91374-21-9 Ropinirole 
• 93189-18-5 N-(7-methoxynaphthalen-1-yl)acetamide 
• 66240-21-9 1-iodo-7-methoxynaphthalene 
• 82995-06-0 3-bromo-1-fluoro-7-hydroxynaphthalene 
• 550998-27-1 8-chloro-2-methoxynaphthalene 
• 5302-79-4 7-methoxynaphthalen-1-amine 
• 13916-98-8 1-fluoro-7-hydroxynaphthalene 
• 13791-03-2 1-fluoro-7-methoxynaphthalene 
• 29921-50-4 8-chloronaphthalen-2-ol 
• 550998-34-0 tert-butyl[(3-bromo-8-chloro-6-(4-methoxyphenyl)-2-naphthyl)oxy]dimethylsilane 
• 550998-46-4 3-bromo-1,8-dichloro-6-(4-methoxyphenyl)-2-naphthol 
• 550998-43-1 1-chloro-8-fluoro-6-(3-fluoro-4-methoxyphenyl)-2-naphthol 

Relevant articles and documents

Method for preparing 8-acetamido-2-naphthol

The invention provides a method for preparing 8-acetamido-2-naphthol and belongs to the technical field of compound preparation methods. The preparation method comprises the following steps: 8-amino-2-naphthalene sulfonic acid and alkali metal hydroxides according to a molar ratio of 1:(3-12), mixing with an organic solvent in an autoclave, and performing alkali fusion at the temperature of 160-320 DEG C and the pressure of 0-1.5MPa so as to prepare 8-amino-2-naphthol; and recovering the organic solvent from the prepared reactants, carrying out an amidation reaction on the prepared 8-amino-2-naphthol and acetic acid or acetic anhydride at the reaction temperature of 20-40 DEG C so as to obtain 8-acetamido-2-naphthol, performing suction filtration, pressing to dry, thereby obtaining the 8-acetamido-2-naphthol. The preparation method is simple in process, less by-products are produced in the reaction, the sulfonate purity is high, the high-purity 8-acetamido-2-naphthol can be directly prepared by alkali fusion without refining, the production cost is reduced, lots of acidic wastewater is not produced, and the environmental protection is facilitated.

New compounds with antiglutamatergic properties and uses thereof

The present invention provides new compounds displaying antiglutamatergic properties. It also provides the use of such compounds for the treatment and/or prophylaxis of conditions and diseases linked to abnormalities in glutamatergic transmission. It further provides a pharmaceutical composition for the treatment and/or prophylaxis of acute and chronic neurodegenerative conditions and disorders.

Synthesis of HKI 0231B

The total synthesis of HKI 0231B (1b) was completed in 12 linear steps and 15.6% overall yield. An unusual anionic cyclization provided access to intermediate 61 and the embedded benz[cd]-indol-3-(1H)-one ring system 3. Directed ortho-lithiation in the presence of a ketone followed by formylation and finally acid-catalyzed methanolysis complete the synthesis. Studies directed toward the construction and reactivity of the lactam acetal functionality present in HKI 0231A (1a) are also reported.