N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine

Base Information

• Chemical Name: N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine
• CAS No.: 503000-58-6
• Molecular Formula: C₂₀H₂₉N₃O
• Molecular Weight: 327.47
• Mol file: 503000-58-6.mol

Synonyms:N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine

Chemical Property of N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine

There total 30 articles about N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine 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:

3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid (503000-34-8) → N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine (503000-58-6)

Guidance literature:

Multi-step reaction with 13 steps

1: (COCl)2 / CH₂Cl₂ / 2 h / 20 °C

2: 454 mg / NH₃ / tetrahydrofuran / 20 °C

3: p-TsOH*H₂O / benzene / 14 h / Heating

4: 152 mg / benzene / 6 h / Heating

5: 99 percent / H₂ / PtO₂ / ethanol / 12 h / 20 °C

6: LiAlH₄ / tetrahydrofuran / 2 h / Heating

7: Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

8: aq. HCl / tetrahydrofuran / 1 h / Heating

9: t-BuOK / benzene; 2-methyl-propan-2-ol / 0.5 h / 20 °C

10: 85 percent / p-TsOH*H₂O / benzene / 14 h / Heating

11: BH₃*THF / tetrahydrofuran / 20 °C

12: aq. HCl / tetrahydrofuran / 1 h / Heating

13: 95.8 mg / Na₂CO₃ / ethanol / 3 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; potassium tert-butylate; ammonia; hydrogen; sodium carbonate; toluene-4-sulfonic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ol034020s

Reference yield:

(4S)-4-(2-carbamoylethyl)-4-vinyl-2-cyclohexene-1-one (503000-35-9) → N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine (503000-58-6)

Guidance literature:

Multi-step reaction with 11 steps

1: p-TsOH*H₂O / benzene / 14 h / Heating

2: 152 mg / benzene / 6 h / Heating

3: 99 percent / H₂ / PtO₂ / ethanol / 12 h / 20 °C

4: LiAlH₄ / tetrahydrofuran / 2 h / Heating

5: Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

6: aq. HCl / tetrahydrofuran / 1 h / Heating

7: t-BuOK / benzene; 2-methyl-propan-2-ol / 0.5 h / 20 °C

8: 85 percent / p-TsOH*H₂O / benzene / 14 h / Heating

9: BH₃*THF / tetrahydrofuran / 20 °C

10: aq. HCl / tetrahydrofuran / 1 h / Heating

11: 95.8 mg / Na₂CO₃ / ethanol / 3 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; borane-THF; potassium tert-butylate; hydrogen; sodium carbonate; toluene-4-sulfonic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ol034020s

Reference yield:

(1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol (503000-53-1) → N-(6a-ethyl-decahydro-pyrrolo[3,2,1-ij]quinolin-9-ylidene)-N'-(2-methoxy-phenyl)-hydrazine (503000-58-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 91 percent / Jones reagent / acetone / 0.33 h / 20 °C

2: (COCl)2 / CH₂Cl₂ / 2 h / 20 °C

3: 454 mg / NH₃ / tetrahydrofuran / 20 °C

4: p-TsOH*H₂O / benzene / 14 h / Heating

5: 152 mg / benzene / 6 h / Heating

6: 99 percent / H₂ / PtO₂ / ethanol / 12 h / 20 °C

7: LiAlH₄ / tetrahydrofuran / 2 h / Heating

8: Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

9: aq. HCl / tetrahydrofuran / 1 h / Heating

10: t-BuOK / benzene; 2-methyl-propan-2-ol / 0.5 h / 20 °C

11: 85 percent / p-TsOH*H₂O / benzene / 14 h / Heating

12: BH₃*THF / tetrahydrofuran / 20 °C

13: aq. HCl / tetrahydrofuran / 1 h / Heating

14: 95.8 mg / Na₂CO₃ / ethanol / 3 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; jones reagent; borane-THF; oxalyl dichloride; potassium tert-butylate; ammonia; hydrogen; sodium carbonate; toluene-4-sulfonic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; acetone; tert-butyl alcohol; benzene; 1: Jones oxidation;

DOI:10.1021/ol034020s

upstream raw materials:

(3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one

2-methoxyphenylhydrazine hydrochloride

3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid

(4S)-4-(2-carbamoylethyl)-4-vinyl-2-cyclohexene-1-one

Downstream raw materials:

(+)-dehydrodeacetylaspidospermine