化工社化工社 化学情報印刷レポート · 研究参考用
Benzenemethanamine, 3,4-dimethyl- → 4-chloro-6-(3,4-dimethyl-benzylamino)-2H-phthalazin-1-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Benzenemethanamine, 3,4-dimethyl- | HCID 66888 | — |
| 反応物 | Binap, (A+-)- | HCID 634876 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 反応物 | 6-Bromo-4-chlorophthalazin-1(2H)-one | HCID 53308487 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | Dimethylacetamide | HCID 31374 | — |
| 生成物 | 4-chloro-6-(3,4-dimethyl-benzylamino)-2H-phthalazin-1-one | HCID 24948530 | 11.6% |
反応手順
A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.578 mmol), 3,4-dimethylbenzylamine (0.09 mL, 0.636 mmol), Pd2(dba)3 (58 mg, 0.063 mmol), rac-BINAP (104 mg, 0.167 mmol) and NaOtBu (155 mg, 1.613 mmol) in DMA (6 mL) was heated at 85° C. for 1.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(3,4-dimethyl-benzylamino)-2H-phthalazin-1-one (21 mg) as a white solid, 1H (400 MHz, d6-DMSO) δ: 2.15 (d, 6H), 4.25 (d, 2H), 6.79 (s, 1H), 7.05 (s, 2H), 7.10 (m, 2H), 7.57 (t, 1H), 7.87 (d, 1H), 12.30 (s, 1H) ppm; m/z (M+1) 313.99.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08044041B2 |
| 出典データセット | uspto-grants-2011_10 |
| ORD ID | ord-d803006664384c7c81e22589b4a1fc65 |
| 出典メモ | uspto-grants-2011_10 |