No renderable structure data available
CC1=CC2=C(O1)C=CC(=C2)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-methyl-1-benzofuran-5-amine |
|---|---|
| IUPAC Name | — |
| CAS Number | 26210-75-3 |
| Database ID | 3157484 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-methyl-1-benzofuran-5-amine (CAS 26210-75-3) 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 3157484
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c9128c9aa92a43f0b854604ceba80e2eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 35° C. mixture of 50 g of 2-methyl-5-nitrobenzofuran, ethanol (250 mL), THF (250 mL) and wet 10% Pd/C (4 g) was added ammonium formate (53.4 g, 0.85 mol) over 50 min. After an additional 4 h, the reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was taken up in methyl t-butyl ether. This mixture was filtered, concentrated and dried to provide 2-methyl-5-benzofuranamine which was converted to its hydrochloride salt or its oxalate salt. The oxalate was prepared as follows: To a solution of 2-methyl-5-benzofuranamine in TBME (415 mL) was added a solution of oxalic acid (25.4 g) in methanol (80 mL) dropwise. The precipitate was stirred for 2 h, collected, washed with methanol/TBME and dried to provide 2-methyl-5-benzofuranamine oxalate. filtered through Celite The filtrate was concentrated This mixture was filtered concentrated dried
Source ID: ord-4ffb5ed6f703406281c914226a9a8566Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 35° C. mixture of 50 g of 2-methyl-5-nitrobenzofuran, ethanol (250 mL), THF (250 mL) and wet 10% Pd/C (4 g) was added ammonium formate (53.4 g, 0.85 mol) over 50 min. After an additional 4 h, the reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was taken up in methyl t-butyl ether. This mixture was filtered, concentrated and dried to provide 2-methyl-5-benzofuranamine which was converted to its hydrochloride salt or its oxalate salt. The oxalate was prepared as follows: To a solution of 2-methyl-5-benzofuranamine in TBME (415 mL) was added a solution of oxalic acid (25.4 g) in methanol (80 mL) dropwise. The precipitate was stirred for 2 h, collected, washed with methanol/TBME and dried to provide 2-methyl-5-benzofuranamine oxalate. filtered through Celite The filtrate was concentrated This mixture was filtered concentrated dried
Source ID: ord-4ffb5ed6f703406281c914226a9a8566Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c9128c9aa92a43f0b854604ceba80e2eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-methyl-5-nitro-benzofuran [19] (125 mg, 0.706 mmol) in methanol (20 mL) was added 5% palladium on carbon (20 mg) and the mixture was stirred under 1 atm H2 for 4 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica plug to afford 5-amino-2-methyl benzofuran as a red-brown oil (78 mg, 75%), single spot at Rf 0.45 (1:1 hexane:ethyl acetate). 1H NMR (CDCl3): δ 7.17 (1H, d, J=8.7 Hz), 6.75 (1H, d, J=2.5 Hz), 6.57 (1H, dd, J8.7, 2.5 Hz), 6.20 (1H, s), 3.53 (2H, s, NH2), 2.39 (3 H, s). The mixture was filtered through celite the filtrate evaporated
Source ID: ord-b83a64d4cb7541459bc136ed55dc81beConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Preparation of title compound. A solution of 2-methyl-5-benzofuranamine (32 mg, 0.22 mmol) and 3,3-bis(methylthio)-2-cyanoacrylamide (41 mg, 0.22 mmol) in ethanol (0.35 mL) was stirred at 80° C. After stirring for 5 h, a solution of 3-aminohexahydro-1-phenylmethyl-2H-azepin-2-one (74 mg, 0.29 mmol) in ethanol (0.74 mL) was added. After stirring at 80° C. for 2 days, the reaction was purified by column chromatography (silica, 1% methanol/dichloromethane) to afford the title compound (37 mg, 37% yield): MS (ESI, pos. ion spectrum) m/z 458; HPLC (method A) tR 4.13 min. After stirring at 80° C. for 2 days the reaction was purified by column chromatography (silica, 1% methanol/dichloromethane)
Source ID: ord-44dae7d193bc481b8840d58d8d9c28f4Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-methyl-5-benzofuranamine (0.24 mmol), 1,1-bis(methylthio)-2-nitroethylene (40 mg, 0.24 mmol) and triethylamine (0.035 mL, 0.25 mmol) in ethanol (0.35 mL) was stirred at 80° C. for 2 h. To the mixture was added 1-[(3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl)acetyl]pyrrolidine (70 mg, 0.24 mmol) and the resulting reaction was stirred at 80° C. overnight. The reaction mixture was purified by column chromatography (silica, 3% methanol/ethyl acetate) to provide the title compound (29 mg, 24% yield): MS (ESI, pos. ion spectrum) m/z 504; HPLC (method A) tR 3.67 min. the resulting reaction The reaction mixture was purified by column chromatography (silica, 3% methanol/ethyl acetate)
Source ID: ord-050b87056bde4874a785b99d82e7810eConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Preparation of title compound. A solution of 2-methyl-5-benzofuranamine (0.24 mmol), 1,1-bis(methylthio-2,2-dicyanoethylene (34 mg, 0.20 mmol) and triethylamine (0.035 mL, 0.25 mmol) in ethanol (0.35 mL) was stirred at 80° C. for 4 h. To the mixture was added 1-[(3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl)acetyl]pyrrolidine (70 mg, 0.24 mmol) and the resulting reaction was stirred at 80° C. overnight. The reaction mixture was purified by column chromatography (silica, 5% methanol/ethyl acetate) to afford the title compound (3 mg, 3% yield): MS (ESI, pos. ion spectrum) m/z 509; HPLC (method A) tR 3.80 min. the resulting reaction The reaction mixture was purified by column chromatography (silica, 5% methanol/ethyl acetate)
Source ID: ord-0ae0cd8413b64588ae4897cb0b3a898cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 35° C. mixture of 50 g of 2-methyl-5-nitrobenzofuran, ethanol (250 mL), THF (250 mL) and wet 10% Pd/C (4 g) was added ammonium formate (53.4 g, 0.85 mol) over 50 min. After an additional 4 h, the reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was taken up in methyl t-butyl ether. This mixture was filtered, concentrated and dried to provide 2-methyl-5-benzofuranamine which was converted to its hydrochloride salt or its oxalate salt. The oxalate was prepared as follows: To a solution of 2-methyl-5-benzofuranamine in TBME (415 mL) was added a solution of oxalic acid (25.4 g) in methanol (80 mL) dropwise. The precipitate was stirred for 2 h, collected, washed with methanol/TBME and dried to provide 2-methyl-5-benzofuranamine oxalate. filtered through Celite The filtrate was concentrated This mixture was filtered concentrated dried
Source ID: ord-4ffb5ed6f703406281c914226a9a8566PubChem References
These sources are listed in the compound's public database record.
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