1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione

Base Information

• Chemical Name: 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione
• CAS No.: 184957-86-6
• Molecular Formula: C₂₄H₂₀N₂O₆S₂
• Molecular Weight: 496.565
• Mol file: 184957-86-6.mol

Synonyms:1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione

Chemical Property of 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione

There total 10 articles about 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione 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: 92.0%

1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-diol → 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione (184957-86-6)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1021/jo961743z

Reference yield:

6,7-dimethoxy-4-methylquinoline (105908-35-8) → 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione (184957-86-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 63 percent / HNO₃ / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min

2: 73 percent / TFA, t-BuI, I₂, FeCl₂ / dimethylsulfoxide / 5 h / 80 - 85 °C

3: 93 percent / HCl / diethyl ether / 65 h / Heating

4: 86 percent / NiCl₂, BaBH₄ / methanol / 0.08 h / 50 °C

5: 67 percent / Et₃N, imidazole / 18 h

6: 70 percent / NaOMe / methanol / 66 h / 50 °C

7: 48 percent / aq. HCl / tetrahydrofuran / 41 h / 80 °C

8: 130 mg / BBr₃, 4 Angstroem sieves / CH₂Cl₂ / 0.83 h / -78 - -20 °C

9: 92 percent / CAN / acetonitrile; H₂O / 0.17 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; iodine; nitric acid; sodium methylate; boron tribromide; tert-Butyl iodide; triethylamine; trifluoroacetic acid; nickel dichloride; iron(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/jo961743z

Reference yield:

4-formyl-6,7-dimethoxy-5-nitroquinoline (159394-51-1) → 1,5-Bis-(toluene-4-sulfonyl)-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinoline-7,8-dione (184957-86-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / HCl / diethyl ether / 65 h / Heating

2: 86 percent / NiCl₂, BaBH₄ / methanol / 0.08 h / 50 °C

3: 67 percent / Et₃N, imidazole / 18 h

4: 70 percent / NaOMe / methanol / 66 h / 50 °C

5: 48 percent / aq. HCl / tetrahydrofuran / 41 h / 80 °C

6: 130 mg / BBr₃, 4 Angstroem sieves / CH₂Cl₂ / 0.83 h / -78 - -20 °C

7: 92 percent / CAN / acetonitrile; H₂O / 0.17 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; sodium methylate; boron tribromide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/jo961743z

upstream raw materials:

6,7-dimethoxy-4-methylquinoline

6,7-dimethoxy-4-methyl-5-nitroquinoline

4-formyl-6,7-dimethoxy-5-nitroquinoline

3,4-dimethoxyaniline

Downstream raw materials:

7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one