HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 4-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 3-Aminophenol | HCID 11568 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloromethyl-7-acetyl-quinoline | HCID 22416851 | — |
| Reactant | 3-(7-Acetyl-2-quinolinylmethoxy)aniline | HCID 22416922 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid | HCID 22416914 | — |
Reaction Steps
3-(7-acetyl-2-quinolinylmethoxy)aniline: 30 mg of NaH (95%) are added at 0° to a solution of 0.13 g of 3-aminophenol in 2.5 ml of DMF and then the batch is stirred for 30 min. at 0°. 0.25 g of 2-chloromethyl-7-acetyl-quinoline in solid form is then added and the batch is stirred for a further one hour at 0° and for another hour at 20°. It is then diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated by evaporation. The evaporation residue is chromatographed on 25 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 85:15 are combined and concentrated by evaporation to give the title compound which is further reacted directly.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05508408 |
| Source dataset | uspto-grants-1996_04 |
| ORD ID | ord-7fd1b0716a154950adb94f29f3060f37 |
| Source note | uspto-grants-1996_04 |