acemetacin tert-butyl ester
acemetacin
Conditions | Yield |
---|---|
With hydrogenchloride; acetic anhydride In acetic acid at 80℃; for 5h; Large scale; | 99.45% |
With trifluoroacetic acid In dichloromethane at 20℃; for 48h; | 80% |
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid tert-butyl ester
acetic acid
acemetacin
Conditions | Yield |
---|---|
With hydrogenchloride; aluminum (III) chloride at 60℃; for 5h; Reagent/catalyst; Temperature; Large scale; | 98.8% |
<1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy>essigsaeurebenzylester
acemetacin
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 80℃; for 24h; Temperature; | 97.8% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 20h; | 95% |
With hydrogen; palladium on activated charcoal In ethyl acetate at 40℃; for 1h; | 93% |
acemetacin tert-butyl ester
A
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
B
acemetacin
Conditions | Yield |
---|---|
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction; | A 30% B 66% |
4-methoxyphenylhydrazine hydrochloride
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
(5-Methoxy-2-methylindol-3-acetoxy)essigsaeurebenzylester
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) K2CO3 / 1.) DMF, 45 min, 50 deg C, 2.) 3 h, 50 deg C 2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) K2CO3 / 1.) DMF, 70 min, 40 deg C, 2.) 4 h, 50 deg C 2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
Laevulinoyloxyessigsaeurebenzylester
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 68 percent / conc. HCl / H2O / 2 h / 20 °C 2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
N-methyl-N-(2-nitrooxyethyl)ammonium nitrate
acemetacin
(N-methyl-N-(2-(nitrooxy)ethyl)carbamoyl)methyl 2-(1-((4-chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetate
Conditions | Yield |
---|---|
With 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; dmap; triethylamine In dichloromethane at 20℃; | 85% |
2-nitroxyethylammonium nitrate
acemetacin
(N-(2-(nitrooxy)ethyl)carbamoyl)methyl 2-(1-((4-chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetate
Conditions | Yield |
---|---|
With 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 2-(Dimethylamino)pyridine | 60% |
{(1R,2R)-cyclohexane-1,2-diamine}dichloridoplatinum(II)
acemetacin
Conditions | Yield |
---|---|
With sodium carbonate; silver nitrate In N,N-dimethyl-formamide at 20℃; for 24h; Darkness; | 53% |
methanol
acemetacin
Conditions | Yield |
---|---|
With tert.-butylnitrite at 40℃; for 48h; Green chemistry; | 48% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide; dmap In DMF (N,N-dimethyl-formamide) at 20℃; for 96h; | 32% |
acemetacin
Conditions | Yield |
---|---|
With oxygen; methylene blue In methanol for 10h; Irradiation; Further byproducts given; | A 24% B 21% C 11% D 21% |
acemetacin
Conditions | Yield |
---|---|
With oxygen; methylene blue In methanol for 10h; Irradiation; Further byproducts given; | A 10% B 21% C 11% D 21% |
acemetacin
B
para-chlorobenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 30℃; Kinetics; Equilibrium constant; Further Variations:; Solvents; detergents; micelles; zwitterionic micelles; | |
With borate buffer at 30℃; pH=9.65; Kinetics; Equilibrium constant; Further Variations:; with/without L-α-phosphatidylcholine vesicles; detergents; micelles; | |
With perchloric acid In water at 25℃; Kinetics; Product distribution; |
acemetacin
A
5-Methoxy-2-methylindole-3-acetic acid
B
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
D
para-chlorobenzoic acid
Conditions | Yield |
---|---|
In water at 30℃; Kinetics; Further Variations:; pH-values; Temperatures; |
acemetacin
4-chloro-N-hydroxybenzamide
Conditions | Yield |
---|---|
Stage #1: acemetacin With sodium hydroxide; hydroxylamine hydrochloride Stage #2: With hydrogenchloride; iron(III) chloride |
acemetacin
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 20 - 35℃; |
1H-imidazole
acemetacin
Conditions | Yield |
---|---|
In methanol; water for 0.416667h; |
Conditions | Yield |
---|---|
In ethanol at 60℃; |
Conditions | Yield |
---|---|
In ethanol at 20 - 40℃; |
acemetacin
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide at 50 - 80℃; for 5h; |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; |
acemetacin
acemetacin (S)-duloxetine salt
Conditions | Yield |
---|---|
Stage #1: Duloxetine; acemetacin In tetrahydrofuran; methanol Stage #2: In di-isopropyl ether at 12℃; for 12h; | |
In tetrahydrofuran; methanol Product distribution / selectivity; |
Acemetacin is a non-steroidal anti-inflammatory drug, used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain.
Acemetacin, a glycolic acid ester of indometacin, acts as a prodrug; in the body, it is metabolized to indometacin, which then acts as an inhibitor of cyclooxygenase, producing the anti-inflammatory effects.
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