No renderable structure data available
CCOC1=CC2=C(C=CC=C2NC(=O)OC(C)(C)C)C=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl N-(7-ethoxynaphthalen-1-yl)carbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 624729-63-1 |
| Database ID | 59731041 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl N-(7-ethoxynaphthalen-1-yl)carbamate (CAS 624729-63-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 59731041
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-51bcde90cf80455ea6b4a131516dc472Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e5c62a1d1ab14857b6a63589ca1461e8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1752ac232a6e4e8ebcc0a60cbd113e5bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-65e9226f83bc46748280f2e50cf8549aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Next, to a solution of tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 167 mmol) in 100 mL anhydrous 1,4-dioxane was added 4N HCl in 1,4-dioxane (100 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. Diisopropyl ether was added to the reaction mixture and the precipitate was filtered. To the obtained solid was added saturated sodium bicarbonate and the product was extracted with ethylacetate. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (7-ethoxy-1-naphthyl)amine (27.0 g, 86.3% yield). the precipitate was filtered To the obtained solid was added saturated sodium bicarbonate the product was extracted with ethylacetate The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure
Source ID: ord-df58c3f36f0d4a8fb2a6fd16218b0d8fConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Next, to a mixture of tert-butyl (7-hydroxy-1-naphthyl)carbamate (64.0 g, 247 mmol) and cesium carbonate (161 g, 493 mmol) in 300 mL anhydrous DMF was added iodoethane (42.3 g, 272 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hours. Water was added to the mixture, and the product was extracted with ethylacetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. To the obtained residue was added diisopropyl ether and the precipitate was collected and dried to afford tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 67.5% yield). the product was extracted with ethylacetate The organic layer was washed with water and brine dried over Na2SO4 filtered concentrated under reduced pressure To the obtained residue was added diisopropyl ether the precipitate was collected dried
Source ID: ord-e1ce4d9ce19b46f2b5d1590c946e4e41Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-51bcde90cf80455ea6b4a131516dc472Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-51bcde90cf80455ea6b4a131516dc472Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the product of Example 1C (14.47 g, 50.4 mmol) in dioxane (30 mL) at 0° C. was added 4N HCl in dioxane (60 mL, 240 mmol). The reaction mixture was stirred at room temperature for 3.5 hours, diluted with 3 volumes of diethyl ether. The resulting dark brown precipitate was collected by filtration. It was then treated with saturated NaHCO3 solution and was extracted with ethyl acetate. The solution was dried over MgSO4, filtered and evaporated in vacuo to yield the title compound (4.88 g, 52%). The resulting dark brown precipitate was collected by filtration It was then treated with saturated NaHCO3 solution was extracted with ethyl acetate The solution was dried over MgSO4 filtered evaporated in vacuo
Source ID: ord-8d3583298bfc4a8f9fcd982086892242Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Next, to a solution of tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 167 mmol) in 100 mL anhydrous 1,4-dioxane was added 4N HCl in 1,4-dioxane (100 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. Diisopropyl ether was added to the reaction mixture and the precipitate was filtered. To the obtained solid was added saturated sodium bicarbonate and the product was extracted with ethylacetate. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (7-ethoxy-1-naphthyl)amine (27.0 g, 86.3% yield). the precipitate was filtered To the obtained solid was added saturated sodium bicarbonate the product was extracted with ethylacetate The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure
Source ID: ord-df58c3f36f0d4a8fb2a6fd16218b0d8fConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Next, to a mixture of tert-butyl (7-hydroxy-1-naphthyl)carbamate (64.0 g, 247 mmol) and cesium carbonate (161 g, 493 mmol) in 300 mL anhydrous DMF was added iodoethane (42.3 g, 272 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hours. Water was added to the mixture, and the product was extracted with ethylacetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. To the obtained residue was added diisopropyl ether and the precipitate was collected and dried to afford tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 67.5% yield). the product was extracted with ethylacetate The organic layer was washed with water and brine dried over Na2SO4 filtered concentrated under reduced pressure To the obtained residue was added diisopropyl ether the precipitate was collected dried
Source ID: ord-e1ce4d9ce19b46f2b5d1590c946e4e41Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Next, to a mixture of tert-butyl (7-hydroxy-1-naphthyl)carbamate (64.0 g, 247 mmol) and cesium carbonate (161 g, 493 mmol) in 300 mL anhydrous DMF was added iodoethane (42.3 g, 272 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hours. Water was added to the mixture, and the product was extracted with ethylacetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. To the obtained residue was added diisopropyl ether and the precipitate was collected and dried to afford tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 67.5% yield). the product was extracted with ethylacetate The organic layer was washed with water and brine dried over Na2SO4 filtered concentrated under reduced pressure To the obtained residue was added diisopropyl ether the precipitate was collected dried
Source ID: ord-e1ce4d9ce19b46f2b5d1590c946e4e41PubChem References
These sources are listed in the compound's public database record.
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