No renderable structure data available
CC(C)(C)C1CC2=CC=CC=C2N1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-tert-butyl-2,3-dihydro-1H-indole |
|---|---|
| IUPAC Name | — |
| CAS Number | 54856-58-5 |
| Database ID | 4642643 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-tert-butyl-2,3-dihydro-1H-indole (CAS 54856-58-5) 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 4642643
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-048384a1ea2841fea7a490b1f6ee45feConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-dadf77be1df048ac89ec8c2d01bcb372Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g ) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH˜8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps). at 0° C carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-b6a05506104e43adbdfe0df4cafdb503Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH˜8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps). at 0° C carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-2d58af2cc49b4dbfa4b1d2b388220a0fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-tert-butylindoline (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 56 mmol) at 0° C. After addition, the reaction mixture was stirred at room temperature for 1 h. The mixture was carefully poured into cracked ice, basified with Na2CO3 to pH 8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitroindoline (4.0 g, 31% over two steps). 1H NMR (300 MHz, CDCl3) δ 7.52 (dd, J=1.8, 8.1 Hz, 1H), 7.30 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 3.76 (t, J=9.6 Hz, 1H), 2.98-3.07 (m, 1H), 2.82-2.91 (m, 1H), 0.91 (s, 9H). at 0° C After addition The mixture was carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-fb95e2f41fce4c4ba40828c89baea29aConditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-tert-butyl-1H-indole (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10° C. The mixture was stirred for 20 minutes at 10° C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step. The mixture was extracted with ethyl acetate The combined organic layers were dried over anhydrous Na2SO4 filtered concentrated under vacuum
Source ID: ord-ab2c26174cdc469a87d4577b84a8c287Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-tert-butyl-1H-indole (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10° C. The mixture was stirred for 20 minutes at 10° C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step. The mixture was extracted with ethyl acetate The combined organic layers were dried over anhydrous Na2SO4 filtered concentrated under vacuum
Source ID: ord-ab2c26174cdc469a87d4577b84a8c287Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-ten-butyl-1H-indole (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH-8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps). at 0° C carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-48720a2f31d9431c9244018f36b6bb15Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-tert-butyl-1H-indole (10 g, 48 mmol) in AcOH (40 mL) was added NaBH4 at 10° C. The mixture was stirred for 20 minutes at 10° C. before being treated dropwise with H2O under ice cooling. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 2-tert-butylindoline (9.8 g), which was used directly in the next step. The mixture was extracted with ethyl acetate The combined organic layers were dried over anhydrous Na2SO4 filtered concentrated under vacuum
Source ID: ord-ef6a4cefa9ac48f09e6df065def70b07Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-tert-butylindoline (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 56 mmol) at 0° C. After addition, the reaction mixture was stirred at room temperature for 1 h. The mixture was carefully poured into cracked ice, basified with Na2CO3 to pH 8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitroindoline (4.0 g, 31% over two steps). 1H NMR (300 MHz, CDCl3) δ 7.52 (dd, J=1.8, 8.1 Hz, 1H), 7.30 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 3.76 (t, J=9.6 Hz, 1H), 2.98-3.07 (m, 1H), 2.82-2.91 (m, 1H), 0.91 (s, 9H). at 0° C After addition The mixture was carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-ebca98e539db4207bbe2e84b5b25250eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g ) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH˜8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps). at 0° C carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-b6a05506104e43adbdfe0df4cafdb503Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH˜8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps). at 0° C carefully poured into cracked ice extracted with ethyl acetate The combined extracts were washed with brine dried over anhydrous Na2SO4 concentrated under vacuum The residue was purified by column chromatography
Source ID: ord-2d58af2cc49b4dbfa4b1d2b388220a0fPubChem References
These sources are listed in the compound's public database record.
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