Product Name

  • Name

    Indacaterol

  • EINECS 691-091-1
  • CAS No. 312753-06-3
  • Density 1.27 g/cm3
  • Solubility
  • Melting Point
  • Formula C24H28N2O3
  • Boiling Point 660.3 °C at 760 mmHg
  • Molecular Weight 392.498
  • Flash Point 353.1 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 312753-06-3 (Indacaterol)
  • Hazard Symbols
  • Synonyms QAB 149;5-[(1R)-2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxyquinolin-2(1H)-one;
  • PSA 85.35000
  • LogP 3.53980

Synthetic route

indacaterol maleate

indacaterol maleate

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With lithium hydroxide monohydrate In methanol at 35℃; for 1h; Reagent/catalyst;99.84%
(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one
435273-75-9

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Stage #1: (R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 2h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In ethanol at 40℃; under 757.576 Torr; for 4h;		97%
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 20℃;85%
With palladium 10% on activated carbon; hydrogen In methanol at 19 - 22℃; for 1h; Inert atmosphere;83%
5-[(1R)-2-[N-benzyl-(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(benzyloxy)-2(1H)-quinolone

5-[(1R)-2-[N-benzyl-(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(benzyloxy)-2(1H)-quinolone

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 20℃;86.2%
With palladium 10% on activated carbon; hydrogen; acetic acid at 40℃; under 15201 Torr; Pressure; Reagent/catalyst; Temperature;
(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one hydrochloride

(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one hydrochloride

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 25 - 30℃; under 2250.23 - 3000.3 Torr; for 4h;85.5%
5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-triethylsilyloxyethyl]-8-(benzyloxy)-2(1H)-quinolone

5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-triethylsilyloxyethyl]-8-(benzyloxy)-2(1H)-quinolone

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid; tetra-n-butylammoniumfluoride trihydrate In methanol at 20℃;84.5%
5-[(1R)-2-[N-benzyl-(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-triethylsilyloxyethyl]-8-(benzyloxy)-2(1H)-quinolone

5-[(1R)-2-[N-benzyl-(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-triethylsilyloxyethyl]-8-(benzyloxy)-2(1H)-quinolone

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid; tetra-n-butylammoniumfluoride trihydrate In methanol at 20℃;83.7%
8-(phenylmethoxy)-5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-(1H)-quinolin-2-one tartrate
753498-33-8

8-(phenylmethoxy)-5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-(1H)-quinolin-2-one tartrate

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol under 225.023 Torr; Inert atmosphere;77%
With 5%-palladium/activated carbon; hydrogen In methanol under 225.023 Torr; Inert atmosphere;77%
5-{2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl}-8-hydroxy-1H-quinolin-2-one

5-{2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl}-8-hydroxy-1H-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With triethylamine In ethanol; hexane at 25℃; Resolution of racemate;49%
(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one benzoic acid salt

(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one benzoic acid salt

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In acetic acid for 2 - 8h;
With hydrogen; 5%-palladium/activated carbon In acetic acid for 2 - 8h;
5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid; -butyl vinyl ether / tetrahydrofuran; toluene / 0.5 h / 20 - 25 °C / Molecular sieve
1.2: 100 °C
2.1: 5%-palladium/activated carbon; hydrogen / methanol / 225.02 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: Chiralcel AS-V / aq. phosphate buffer; acetonitrile / 25 °C / Resolution of racemate
3.1: 5%-palladium/activated carbon; hydrogen / ethanol / 2 h / 20 °C
3.2: 4 h / 40 °C / 757.58 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 - 40 °C / 757.58 Torr
3.1: triethylamine / ethanol; hexane / 25 °C / Resolution of racemate
View Scheme
Multi-step reaction with 4 steps
1: sodium cyanoborohydride / ethanol / 4 h / -25 - 80 °C / Inert atmosphere
2: sodium carbonate; potassium iodide / acetonitrile / 24 h / -25 - 80 °C
3: (-)-diisopinocamphenylborane chloride / dichloromethane; tetrahydrofuran / 25 h / 10 - 20 °C
4: hydrogen; acetic acid; palladium 10% on activated carbon / 40 °C / 15201 Torr
View Scheme
Multi-step reaction with 4 steps
1: butan-1-ol / 3 h / 100 - 110 °C
2: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 0 - 3 °C / Inert atmosphere
3: potassium carbonate / water; methanol / 1 h
4: acetic acid; palladium 10% on activated carbon; hydrogen / methanol / 6 h / 0 - 8 °C / 750.08 - 1500.15 Torr / Inert atmosphere
View Scheme
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
530084-79-8

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid; -butyl vinyl ether / tetrahydrofuran; toluene / 0.5 h / 20 - 25 °C / Molecular sieve
1.2: 100 °C
2.1: 5%-palladium/activated carbon; hydrogen / methanol / 225.02 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: 1H-imidazole / chloroform / 10 h / 25 °C / Reflux
2.1: 1-methyl-pyrrolidin-2-one / 12 h / 95 - 100 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 50 - 55 °C
3.2: 1 h / 25 - 30 °C
4.1: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 - 30 °C / 2250.23 - 3000.3 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 90 °C
2.1: hydrazine hydrate / ethanol / 6 h / Reflux
2.2: 80 °C
3.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
4.1: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
5-(2,2-Dihydroxyacetyl)-8-(benzyloxy)-carbostyril
100331-91-7

5-(2,2-Dihydroxyacetyl)-8-(benzyloxy)-carbostyril

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: Chiralcel AS-V / aq. phosphate buffer; acetonitrile / 25 °C / Resolution of racemate
3.1: 5%-palladium/activated carbon; hydrogen / ethanol / 2 h / 20 °C
3.2: 4 h / 40 °C / 757.58 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 - 40 °C / 757.58 Torr
3.1: triethylamine / ethanol; hexane / 25 °C / Resolution of racemate
View Scheme
5-[2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one

5-[2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 - 40 °C / 757.58 Torr
2: triethylamine / ethanol; hexane / 25 °C / Resolution of racemate
View Scheme
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one
100331-89-3

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran / 0 - 30 °C / Inert atmosphere
1.2: 0 - 30 °C
2.1: 1H-imidazole / chloroform / 10 h / 25 °C / Reflux
3.1: 1-methyl-pyrrolidin-2-one / 12 h / 95 - 100 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 50 - 55 °C
4.2: 1 h / 25 - 30 °C
5.1: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 - 30 °C / 2250.23 - 3000.3 Torr
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 1.33 h / 50 °C
2.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / dichloromethane; toluene; tetrahydrofuran / 2 h / -10 °C
3.1: hydrazine hydrate / ethanol / 6 h / Reflux
3.2: 80 °C
4.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
5.1: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one
530084-74-3

(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-methyl-pyrrolidin-2-one / 12 h / 95 - 100 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 50 - 55 °C
2.2: 1 h / 25 - 30 °C
3.1: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 - 30 °C / 2250.23 - 3000.3 Torr
View Scheme
(R)-8-(benzyloxy)-5-[1-((tert-butyldimethylsilyl)oxy)-2-((5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino)ethyl]quinolin-2(1H)-one

(R)-8-(benzyloxy)-5-[1-((tert-butyldimethylsilyl)oxy)-2-((5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino)ethyl]quinolin-2(1H)-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 50 - 55 °C
1.2: 1 h / 25 - 30 °C
2.1: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 - 30 °C / 2250.23 - 3000.3 Torr
View Scheme
N-benzyl-5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-79-0

N-benzyl-5,6-diethyl-2,3-dihydro-1H-inden-2-amine

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium carbonate; potassium iodide / acetonitrile / 24 h / -25 - 80 °C
2: (-)-diisopinocamphenylborane chloride / dichloromethane; tetrahydrofuran / 25 h / 10 - 20 °C
3: hydrogen; acetic acid; palladium 10% on activated carbon / 40 °C / 15201 Torr
View Scheme
Multi-step reaction with 2 steps
1: triethylamine; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C
2: acetic acid; 5%-palladium/activated carbon; hydrogen; tetra-n-butylammoniumfluoride trihydrate / methanol / 20 °C
View Scheme
5-{2-[N-benzyl(5,6-diethyl-2,3-dihydro-1H-indan-2-yl)amino]acetyl}-8-(benzyloxy)-1H-quinolin-2-one

5-{2-[N-benzyl(5,6-diethyl-2,3-dihydro-1H-indan-2-yl)amino]acetyl}-8-(benzyloxy)-1H-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (-)-diisopinocamphenylborane chloride / dichloromethane; tetrahydrofuran / 25 h / 10 - 20 °C
2: hydrogen; acetic acid; palladium 10% on activated carbon / 40 °C / 15201 Torr
View Scheme
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
530084-79-8

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C
2: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol / 20 °C
View Scheme
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
530084-79-8

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

N-benzyl-5,6-diethyl-2,3-dihydro-1H-inden-2-amine
312753-79-0

N-benzyl-5,6-diethyl-2,3-dihydro-1H-inden-2-amine

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C
2: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol / 20 °C
View Scheme
Reaxys ID: 32936244

Reaxys ID: 32936244

indacaterol
312753-06-3

indacaterol

Reaxys ID: 32936246

Reaxys ID: 32936246

indacaterol
312753-06-3

indacaterol

Reaxys ID: 32936247

Reaxys ID: 32936247

indacaterol
312753-06-3

indacaterol

2-chloro-5,6-diethylindan

2-chloro-5,6-diethylindan

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
2: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
5-(2-phthalimido-1-oxo-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one

5-(2-phthalimido-1-oxo-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / dichloromethane; toluene; tetrahydrofuran / 2 h / -10 °C
2.1: hydrazine hydrate / ethanol / 6 h / Reflux
2.2: 80 °C
3.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
4.1: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
5-(R)-(2-amino-1-hydroxy-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one
774222-23-0

5-(R)-(2-amino-1-hydroxy-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
2: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
5-(R)-(2-phthalimido-1-hydroxy-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one

5-(R)-(2-phthalimido-1-hydroxy-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrazine hydrate / ethanol / 6 h / Reflux
1.2: 80 °C
2.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
3.1: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
5-acetyl-8-hydroxy-2(1H)-quinolinone
62978-73-8

5-acetyl-8-hydroxy-2(1H)-quinolinone

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 2.5 h / 20 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C
2.2: 2.75 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C
3.2: 1.33 h / 50 °C
4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / dichloromethane; toluene; tetrahydrofuran / 2 h / -10 °C
5.1: hydrazine hydrate / ethanol / 6 h / Reflux
5.2: 80 °C
6.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
7.1: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
5-acetyl-8-benzyloxy-1H-quinolin-2-one
93609-84-8

5-acetyl-8-benzyloxy-1H-quinolin-2-one

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C
1.2: 2.75 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C
2.2: 1.33 h / 50 °C
3.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / dichloromethane; toluene; tetrahydrofuran / 2 h / -10 °C
4.1: hydrazine hydrate / ethanol / 6 h / Reflux
4.2: 80 °C
5.1: N-ethyl-N,N-diisopropylamine; sodium iodide / N,N-dimethyl-formamide / 20 - 90 °C
6.1: acetic acid; 5%-palladium/activated carbon; hydrogen / methanol
View Scheme
C31H34N2O3*BrH

C31H34N2O3*BrH

indacaterol
312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / water; methanol / 1 h
2: acetic acid; palladium 10% on activated carbon; hydrogen / methanol / 6 h / 0 - 8 °C / 750.08 - 1500.15 Torr / Inert atmosphere
View Scheme
indacaterol
312753-06-3

indacaterol

succinic acid
110-15-6

succinic acid

Indacaterol succinate

Indacaterol succinate

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 80℃; for 18.0833h;96.3%
indacaterol
312753-06-3

indacaterol

malonic acid
141-82-2

malonic acid

Indacaterol malonate

Indacaterol malonate

Conditions
ConditionsYield
In butan-1-ol at 20 - 80℃; for 18.25h;95.28%
indacaterol
312753-06-3

indacaterol

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Indacaterol tosylate

Indacaterol tosylate

Conditions
ConditionsYield
In ethyl acetate at 20 - 60℃;94.8%
indacaterol
312753-06-3

indacaterol

acetic acid
64-19-7

acetic acid

Indacaterol acetate

Indacaterol acetate

Conditions
ConditionsYield
In dichloromethane; ethyl acetate; isopropyl alcohol at 5 - 35℃; for 11h; Temperature; Solvent;93.73%
In isopropyl alcohol at 20 - 80℃; for 17h;84.9%
indacaterol
312753-06-3

indacaterol

maleic acid
110-16-7

maleic acid

indacaterol maleate

indacaterol maleate

Conditions
ConditionsYield
In isopropyl alcohol for 1h; Reflux;92.5%
In ethanol at 60℃; for 0.166667h;83%
In ethanol at 50 - 60℃;
indacaterol
312753-06-3

indacaterol

methanesulfonic acid
75-75-2

methanesulfonic acid

Indacaterol mesylate

Indacaterol mesylate

Conditions
ConditionsYield
In water at 20 - 70℃; for 20.2h;86.9%
indacaterol
312753-06-3

indacaterol

Indacaterol sulfate

Indacaterol sulfate

Conditions
ConditionsYield
With sulfuric acid; acetic acid at 20 - 50℃; for 18.0833h;86.9%
indacaterol
312753-06-3

indacaterol

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one fumarate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one fumarate

Conditions
ConditionsYield
In methanol at 20 - 50℃; for 3.33333h;86.4%
indacaterol
312753-06-3

indacaterol

L-Tartaric acid
87-69-4

L-Tartaric acid

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one L-tartrate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one L-tartrate

Conditions
ConditionsYield
In isopropyl alcohol at 50℃; for 15h;84.27%
indacaterol
312753-06-3

indacaterol

Indacaterol hydrochloride

Indacaterol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20 - 50℃; for 17h;84.27%
indacaterol
312753-06-3

indacaterol

Indacaterol hydrobromide

Indacaterol hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In methanol at 20 - 50℃; for 3.25h;84.27%
indacaterol
312753-06-3

indacaterol

formic acid
64-18-6

formic acid

Indacaterol formate

Indacaterol formate

Conditions
ConditionsYield
In methanol at 25 - 50℃; for 15h;79.37%
indacaterol
312753-06-3

indacaterol

1-hydroxy-2-naphthoic acid
86-48-6

1-hydroxy-2-naphthoic acid

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one xinafoate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one xinafoate

Conditions
ConditionsYield
In butan-1-ol at 20 - 100℃; for 17h;76%
indacaterol
312753-06-3

indacaterol

Hippuric Acid
495-69-2

Hippuric Acid

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one hippurate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one hippurate

Conditions
ConditionsYield
In methanol at 20 - 50℃; for 4.16667h;75.7%
indacaterol
312753-06-3

indacaterol

glycolic Acid
79-14-1

glycolic Acid

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one glycolate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one glycolate

Conditions
ConditionsYield
In methanol at 20 - 50℃;71.37%
indacaterol
312753-06-3

indacaterol

ethanesulfonic acid
594-45-6

ethanesulfonic acid

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one esylate

(R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one esylate

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 20 - 50℃;
indacaterol
312753-06-3

indacaterol

[Br]QAB149

[Br]QAB149

Conditions
ConditionsYield
With bromine In acetic acid at 20℃; for 1h;
indacaterol
312753-06-3

indacaterol

[3H]QAB149

[3H]QAB149

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine / acetic acid / 1 h / 20 °C
2: palladium 10% on activated carbon; tritium; triethylamine / 5 h / 20 °C
View Scheme
indacaterol
312753-06-3

indacaterol

C24H30N2O3
1403389-05-8

C24H30N2O3

Conditions
ConditionsYield
With 10% Pd/C; hydrogen at 25℃; under 760.051 Torr; for 360h;
indacaterol
312753-06-3

indacaterol

C24H27ClN2O2

C24H27ClN2O2

Conditions
ConditionsYield
With thionyl chloride In acetonitrile for 0.0833333h; Reflux;
indacaterol
312753-06-3

indacaterol

5-[2-(5,6-diethyl-indan-2-ylamino)-ethyl]-8-hydroxy-1H-quinolin-2-one

5-[2-(5,6-diethyl-indan-2-ylamino)-ethyl]-8-hydroxy-1H-quinolin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride / acetonitrile / 0.08 h / Reflux
2.1: sodium tetrahydroborate / ethanol / 18 h / 25 °C
2.2: 2 h / Reflux
View Scheme

Indacaterol Specification

The 2(1H)-Quinolinone,5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-, with the CAS registry number 312753-06-3, is also known as 5-(2-(5,6-Diethylindan-2-ylamino)-1-hydroxyethyl)-8-hydroxy-1H-quinolin-2-one. This chemical's molecular formula is C24H28N2O3 and molecular weight is 392.49072. Its IUPAC name is called 5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one. This chemical's classification code is Treatment of COPD.

Physical properties of 2(1H)-Quinolinone,5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-: (1)ACD/LogP: 3.88; (2)ACD/LogD (pH 5.5): 0.99; (3)ACD/LogD (pH 7.4): 2.45; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 19.5; (6)ACD/KOC (pH 5.5): 3.96; (7)ACD/KOC (pH 7.4): 114.74; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 8; (11)Index of Refraction: 1.659; (12)Molar Refractivity: 113.26 cm3; (13)Molar Volume: 306.8 cm3; (14)Surface Tension: 63.9 dyne/cm; (15)Density: 1.27 g/cm3; (16)Flash Point: 353.1 °C; (17)Enthalpy of Vaporization: 102.09 kJ/mol; (18)Boiling Point: 660.3 °C at 760 mmHg; (19)Vapour Pressure: 2.47E-18 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCC1=C(C=C2CC(CC2=C1)NCC(C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC
(2)Isomeric SMILES: CCC1=C(C=C2CC(CC2=C1)NC[C@@H](C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC
(3)InChI: InChI=1S/C24H28N2O3/c1-3-14-9-16-11-18(12-17(16)10-15(14)4-2)25-13-22(28)19-5-7-21(27)24-20(19)6-8-23(29)26-24/h5-10,18,22,25,27-28H,3-4,11-13H2,1-2H3,(H,26,29)/t22-/m0/s1
(4)InChIKey: QZZUEBNBZAPZLX-QFIPXVFZSA-N

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