4H-Imidazo[4,5,1-ij]quinolin-5-amine,5,6-dihydro-N-methyl-,(R)-(9CI)

Base Information

• Chemical Name: 4H-Imidazo[4,5,1-ij]quinolin-5-amine,5,6-dihydro-N-methyl-,(R)-(9CI)
• CAS No.: 185943-30-0
• Molecular Formula: C₁₁H₁₃N₃
• Molecular Weight: 187.244
• Mol file: 185943-30-0.mol

Synonyms:4H-Imidazo[4,5,1-ij]quinolin-5-amine,5,6-dihydro-N-methyl-, (R)- (9CI)

Chemical Property of 4H-Imidazo[4,5,1-ij]quinolin-5-amine,5,6-dihydro-N-methyl-,(R)-(9CI)

Chemical Property:

• PSA: 29.85000
• LogP: 1.57130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-Imidazo[4,5,1-ij]quinolin-5-amine,5,6-dihydro-N-methyl-,(R)-(9CI)

There total 13 articles about 4H-Imidazo[4,5,1-ij]quinolin-5-amine,5,6-dihydro-N-methyl-,(R)-(9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Benzyl-(R)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-5-yl-methyl-amine (185943-27-5) → (R)-5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-5-yl-methyl-amine (185943-30-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 55 ℃; for 18h; under 2585.7 Torr;

DOI:10.1021/jm960360q

Reference yield:

quinoline (91-22-5) → (R)-5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-5-yl-methyl-amine (185943-30-0)

Guidance literature:

Multi-step reaction with 12 steps

1: DIBAL-H / toluene; tetrahydrofuran / 45 °C

2: Et₃N / toluene; tetrahydrofuran / 1 h / 45 °C

3: 65 percent / N-bromosuccinimide, H₂O / dimethylsulfoxide / 0.17 h / 20 - 30 °C

4: H₂O / ethanol / 3 h / Heating

6: 4.62 g / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 0.67 h

7: 3.45 g / H₂ / 10percent Pd/C / ethanol / 1 h

8: 3.68 g / Na₂CO₃ / dimethylformamide / 1 h

9: 1.) sec-butyllithium, 2.) tosyl azide / 1.) cyclohexane, THF, -78 deg C, 15 min, 2.) cyclohexane, THF, RT, 1 h

10: 1.97 g / H₂ / 10percent Pd/C / ethanol / 0.75 h / 2585.7 Torr

11: 1.43 g / 1 h / 110 °C

12: H₂ / 10percent Pd/C / ethanol / 18 h / 55 °C / 2585.7 Torr

With N-Bromosuccinimide; 4-toluenesulfonyl azide; water; hydrogen; sec.-butyllithium; diisobutylaluminium hydride; sodium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm960360q

Reference yield:

1,2-dihydroquinoline (612-18-0) → (R)-5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-5-yl-methyl-amine (185943-30-0)

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / toluene; tetrahydrofuran / 1 h / 45 °C

2: 65 percent / N-bromosuccinimide, H₂O / dimethylsulfoxide / 0.17 h / 20 - 30 °C

3: H₂O / ethanol / 3 h / Heating

5: 4.62 g / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 0.67 h

6: 3.45 g / H₂ / 10percent Pd/C / ethanol / 1 h

7: 3.68 g / Na₂CO₃ / dimethylformamide / 1 h

8: 1.) sec-butyllithium, 2.) tosyl azide / 1.) cyclohexane, THF, -78 deg C, 15 min, 2.) cyclohexane, THF, RT, 1 h

9: 1.97 g / H₂ / 10percent Pd/C / ethanol / 0.75 h / 2585.7 Torr

10: 1.43 g / 1 h / 110 °C

11: H₂ / 10percent Pd/C / ethanol / 18 h / 55 °C / 2585.7 Torr

With N-Bromosuccinimide; 4-toluenesulfonyl azide; water; hydrogen; sec.-butyllithium; sodium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm960360q

upstream raw materials:

Benzyl-(R)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-5-yl-methyl-amine

quinoline

1,2-dihydroquinoline

1-tert-butyloxycarbonyl-1,2-dihydroquinoline