• Name

  2-Hydroxy-3-naphtoamide

• EINECS 222-926-6
• CAS No. 3665-51-8
• Article Data16
• CAS DataBase
• Density 1.33g/cm³
• Solubility
• Melting Point 211-216 ºC
• Formula C11H9 N O2
• Boiling Point 426.4°Cat760mmHg
• Molecular Weight 187.198
• Flash Point 211.7°C
• Transport Information
• Appearance
• Safety Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NO_x.
• Risk Codes R36/37/38   
• Molecular Structure
• Hazard Symbols
• Synonyms 2-Naphthamide,3-hydroxy- (6CI,7CI,8CI); 2-Hydroxy-3-naphthalenecarboxamide;2-Hydroxy-3-naphthamide; 2-Hydroxy-3-naphthoamide; 2-Hydroxy-3-naphthoic acidamide; 3-Hydroxy-2-naphthalenecarboxamide; 3-Hydroxy-2-naphthamide; NSC 37060
• PSA 63.32000
• LogP 2.34460

Synthetic route

53855-64-4

3-acetoxy-2-naphthoyl chloride

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With ammonium hydroxide In dichloromethane for 24h; Ambient temperature;	95%

92-70-6

3-Hydroxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With phosphoric acid; urea at 180℃; for 2h;	90%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 1h;	72%
Multi-step reaction with 2 steps 1: HCl 2: alcoholic ammonia / 170 °C / im geschlossenen Rohr View Scheme
Multi-step reaction with 5 steps 1: concentrated sulfuric acid 2: thionyl chloride; benzene / Einleiten von Ammoniak in das Reaktionsgemisch 3: thionyl chloride 4: methanolic KOH-solution 5: concentrated sulfuric acid / 0 °C View Scheme

52449-77-1

3-hydroxy-2-naphthonitrile

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With sulfuric acid at 0℃;

7163-25-9

ethyl 3-hydroxy-2-naphthanoate

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With ammonia at 170℃; im geschlossenen Rohr;
With ammonium sulfite; ammonia at 125℃; im geschlossenen Rohr;

1734-00-5

3-hydroxy-2-naphthoyl chloride

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With ammonia; benzene

13042-06-3

3-methoxy-[2]naphthoic acid amide

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid

92616-44-9

3-methoxy-2-naphthonitrile

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid

57-13-6

urea

92-70-6

3-Hydroxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With phosphoric acid

5464-07-3

3-acetoxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / oxalyl chloride, DMF / toluene / 1 h / Ambient temperature 2: 95 percent / conc. NH4OH / CH2Cl2 / 24 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: thionyl chloride; benzene / Einleiten von Ammoniak in das Reaktionsgemisch 2: thionyl chloride 3: methanolic KOH-solution 4: concentrated sulfuric acid / 0 °C View Scheme

92-70-6

3-Hydroxy-2-naphthoic acid

disulfite

disulfite

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / conc. H2SO4 / 0.08 h / Heating 2: 97 percent / oxalyl chloride, DMF / toluene / 1 h / Ambient temperature 3: 95 percent / conc. NH4OH / CH2Cl2 / 24 h / Ambient temperature View Scheme

3-acetoxy-[2]naphthonitrile

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanolic KOH-solution 2: concentrated sulfuric acid / 0 °C View Scheme

175293-41-1

3-carbamoylnaphthalen-2-yl acetate

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride 2: methanolic KOH-solution 3: concentrated sulfuric acid / 0 °C View Scheme

79-37-8

oxalyl dichloride

concentrated NH4 OH

concentrated NH4 OH

5464-07-3

3-acetoxy-2-naphthoic acid

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide; toluene

...Expand

883-99-8

3-hydroxy-2-naphthoic acid methyl ester

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

Conditions

Conditions	Yield
With ammonia In methanol at 60℃; for 24h; Sealed tube;

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

98-59-9

p-toluenesulfonyl chloride

3-(toluene-4-sulfonyloxy)-[2]naphthoic acid amide

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 10℃; for 0.5h;	96%
With alkali

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

7377-26-6

4-Methoxycarbonylbenzoyl chloride

1257228-07-1

C20H15NO5

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 24h;	94%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

108-94-1

cyclohexanone

68158-67-8

spiro[cyclohexane-1,2'-naphtho[2,3-e][1,3]oxazin]-4'(3'H)-one

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 8h; Reflux;	92%

75-30-9

2-iodo-propane

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

3-isopropoxy-2-naphthamide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 2h; Inert atmosphere;	92%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

98-53-3

4-tercbutyl-cyclohexanone

4-tert-butylspiro[cyclohexane-1,2'-naphtho[2,3-e][1,3]oxazin]-4'(3'H)-one

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 8h; Reflux;	91%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

589-92-4

1-methylcyclohexan-4-one

4-methylspiro[cyclohexane-1,2'-naphtho[2,3-e][1,3]oxazin]-4'(3'H)-one

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 8h; Reflux;	88%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

16587-71-6

4-tert-amylcyclohexanone

4-(1,1-dimethylpropyl)spiro[cyclohexane-1,2'-naphtho[2,3-e][1,3]oxazin]-4'(3'H)-one

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 8h; Reflux;	85%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

120-92-3

cyclopentanone

68158-68-9

spiro[cyclopentane-1,2'-naphtho[2,3-e][1,3]oxazin]-4'(3'H)-one

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 8h; Reflux;	80%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

108-24-7

acetic anhydride

175293-41-1

3-carbamoylnaphthalen-2-yl acetate

Conditions

Conditions	Yield
With pyridine at 20℃;	80%
With pyridine for 0.5h; Ambient temperature;	74%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

502-42-1

cycloheptanone

spiro[cycloheptane-1,2'-naphtho[2,3-e][1,3]oxazin]-4'(3'H)-one

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 8h; Reflux;	78%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

69-72-7

salicylic acid

24798-60-5

2-(3-hydroxynaphthalen-2-yl)-4H-benzo[e][1,3]oxazin-4-one

Conditions

Conditions	Yield
With pyridine; thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene for 4.5h;	53%

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

1204345-48-1

N-[(4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone

1204345-19-6

1'-[(4,8-dimethoxyquinolin-2-yl)carbonyl]spiro[2H-naphtho[2,3-e]-1,3-oxazin-2,4'-piperidin]-4-(3H)-one

Conditions

Conditions	Yield
With morpholine In methanol; toluene for 20h; Reflux;	27%

109-65-9

1-bromo-butane

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

109535-42-4

3-butoxy-[2]naphthoic acid amide

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

16173-26-5

3-(4,5-dihydro-1H-imidazol-2-yl)-naphthalen-2-ol

Conditions

Conditions	Yield
With ethylenediamine at 180℃;

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

541-41-3

chloroformic acid ethyl ester

53653-44-4

2H-Naphtho<2,3-e>-1,3-oxazin-2,4(3H)-dion

Conditions

Conditions	Yield
With pyridine

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

108-24-7

acetic anhydride

73388-42-8

(3-acetoxy-[2]naphthoyl)-acetyl-amine

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

105-36-2

ethyl bromoacetate

100727-60-4

(3-carbamoyl-[2]naphthyloxy)-acetic acid

Conditions

Conditions	Yield
anschliessend Erwaermen mit wss. NaOH;

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

75-36-5

acetyl chloride

175293-41-1

3-carbamoylnaphthalen-2-yl acetate

Conditions

Conditions	Yield
With pyridine

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

98-09-9

benzenesulfonyl chloride

3-benzenesulfonyloxy-[2]naphthoic acid amide

Conditions

Conditions	Yield
With alkali

104-53-0

3-phenyl-propionaldehyde

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

68158-53-2

2-phenethyl-2,3-dihydro-naphtho[2,3-e][1,3]oxazin-4-one

878-00-2

4-formylphenyl acetate

3665-51-8

3-hydroxy-2-naphthalenecarboxamide

68158-60-1

2-(4-acetoxy-phenyl)-2,3-dihydro-naphtho[2,3-e][1,3]oxazin-4-one

2-Hydroxy-3-naphtoamide Chemical Properties

2-Hydroxy-3-naphtoamide Uses

2-Hydroxy-3-naphtoamide Toxicity Data With Reference

2-Hydroxy-3-naphtoamide Consensus Reports

2-Hydroxy-3-naphtoamide Safety Profile