dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Base Information

Chemical Name:dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester
CAS No.:474296-04-3
Molecular Formula:C₂₁H₂₃N₃O₅
Molecular Weight:397.431
Hs Code.:

dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1<i>H</i>-benzo[<i>c</i>]azepin-7-yl ester

Synonyms:dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

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Chemical Property of dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Chemical Property:

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Technology Process of dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

There total 13 articles about dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester 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:

: 52085-14-0
4-benzoxy-salicylaldehyde

: 474296-04-3
dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 79 percent / diisopropylethylamine / CH₂Cl₂ / 18 h / 20 °C

2: 99 percent / NaH / tetrahydrofuran / 2 h / 0 °C

3: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4: H₂; acetic acid / Pd(OH)2/C / methanol; H₂O / 20 °C

5: triethylamine / methanol / 20 °C

6: potassium carbonate / dimethylformamide / 20 °C

7: LiAlH₄ / tetrahydrofuran / -50 - 0 °C

8: diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 20 °C

9: conc. HCl / H₂O; methanol / 20 °C

10: triethylamine / methanol / 20 °C

11: pyridine / CH₂Cl₂ / 0 °C

12: tetrakis(triphenylphosphine)palladium⁽⁰⁾; lithium chloride; 2,6-di-tert-butyl-phenol / dioxane / 100 °C

13: sodium hydride / dimethylformamide / 0 - 20 °C

14: (1,3-dimesitylimidazolidin-2-yl)(PCy₃)Ru(Cl)2(=CHPh) / CH₂Cl₂ / 45 °C

15: HCl / ethyl acetate / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,6-di-tert-butylphenol; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2: Horner-Emmons reaction / 8: Mitsunobu reaction / 12: Stille reaction;
DOI:10.1021/ol026418e

Reference yield:

: 7-dimethylcarbamoyloxy-1-[2-(4-nitro-phenoxy)-ethyl]-1,3-dihydro-benzo[c]azepine-2-carboxylic acid tert-butyl ester

: 474296-04-3
dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Guidance literature:: With hydrogenchloride; In ethyl acetate; at 20 ℃; for 18h;
DOI:10.1016/S0968-0896(03)00452-8

Reference yield:

: 474295-91-5
4-benzyloxy-2-(methoxymethoxy)benzaldehyde

: 474296-04-3
dimethyl-carbamic acid 1-[2-(4-nitro-phenoxy)-ethyl]-2,3-dihydro-1H-benzo[c]azepin-7-yl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 99 percent / NaH / tetrahydrofuran / 2 h / 0 °C

2: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3: H₂; acetic acid / Pd(OH)2/C / methanol; H₂O / 20 °C

4: triethylamine / methanol / 20 °C

5: potassium carbonate / dimethylformamide / 20 °C

6: LiAlH₄ / tetrahydrofuran / -50 - 0 °C

7: diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 20 °C

8: conc. HCl / H₂O; methanol / 20 °C

9: triethylamine / methanol / 20 °C

10: pyridine / CH₂Cl₂ / 0 °C

11: tetrakis(triphenylphosphine)palladium⁽⁰⁾; lithium chloride; 2,6-di-tert-butyl-phenol / dioxane / 100 °C

12: sodium hydride / dimethylformamide / 0 - 20 °C

13: (1,3-dimesitylimidazolidin-2-yl)(PCy₃)Ru(Cl)2(=CHPh) / CH₂Cl₂ / 45 °C

14: HCl / ethyl acetate / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,6-di-tert-butylphenol; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Horner-Emmons reaction / 7: Mitsunobu reaction / 11: Stille reaction;
DOI:10.1021/ol026418e