1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione

Base Information

• Chemical Name: 1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione
• CAS No.: 1224640-11-2
• Molecular Formula: C₁₁H₁₀N₂O₃
• Molecular Weight: 218.212
• Mol file: 1224640-11-2.mol

Synonyms:

Chemical Property of 1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione

There total 1 articles about 1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-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:

N-cyclopropyl-N-(2-nitro-phenyl)-oxalamic acid methyl ester (1224640-10-1) → 1-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-2,3-dione (1224640-12-3) + 1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione (1224640-11-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 2h; under 900.09 Torr; Overall yield = 84 %; Overall yield = 31.2 g;

DOI:10.1002/cmdc.201200474

Reference yield:

1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione (1224640-11-2) → 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzamide (1315469-13-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triphenylphosphine / N,N-dimethyl-formamide / 4 h / 135 °C

2.1: borane-THF / tetrahydrofuran / 20 °C

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 17 h / 20 °C

4.1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / ethyl acetate / 20 h / 120 °C / 52505.3 Torr

5.1: water; lithium hydrochloride monohydrate / 1,4-dioxane / 1.5 h / 20 °C

5.2: pH 1

6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium chloride / N,N-dimethyl-formamide / 20 °C

With borane-THF; lithium hydrochloride monohydrate; water; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

1-cyclopropyl-4-hydroxy-1,2,3,4-tetrahydroquinoxaline-2,3-dione (1224640-11-2) → 2,5-dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoic acid (1315469-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine / N,N-dimethyl-formamide / 4 h / 135 °C

2: borane-THF / tetrahydrofuran / 20 °C

3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C

4: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / ethyl acetate / 100 °C / 67506.8 Torr

5: water; lithium hydrochloride monohydrate / 1,4-dioxane / 4 h / 20 °C

With borane-THF; lithium hydrochloride monohydrate; water; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

N-cyclopropyl-N-(2-nitro-phenyl)-oxalamic acid methyl ester

Downstream raw materials:

1-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-2,3-dione

1-cyclopropyl-1,2,3,4-tetrahydro-quinoxaline

[4-(2,5-dichloro-4-bromophenoxy)pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)methanone

2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester