HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzene, 2-fluoro-4-methyl-1-nitro- → 3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzene, 2-fluoro-4-methyl-1-nitro- | HCID 67966 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Hexanoic acid, 3-amino-, ethyl ester, hydrochloride (1:1) | HCID 75530735 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(5-Methyl-2-nitro-phenylamino)-hexanoic acid ethyl ester | HCID 59497626 | 73.2% |
Reaction Steps
To a solution of 3-Fluoro-4-nitrotoluene (1.0 g, 6.5 mmol) in DMF (5 mL) were: 3-Amino-hexanoic acid ethyl ester hydrochloride (1.3 g, 6.7 mmol) and DIPEA (2.2 mL, 12.9 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by Combiflash using hexane and ethyl acetate (10% gradient) as an eluent to afford 1.4 g of the desired product as orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150556B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-836a387586724ecdb604e6f9f56de0bf |
| Source note | uspto-grants-2015_10 |