関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Ethyl formate | HCID 8025 | — |
| 反応物 | Sodium ethoxide | HCID 2723922 | — |
| 反応物 | 1-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone | HCID 22667147 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | HCID 178486758 | HCID 178486758 | 72.4% |
反応手順
Sodium ethoxide (74.8 g, 1.1 mol) was added to a solution of 1-(2-amino-4-benzyloxy-5-methoxyphenyl)ethanone (29.3 g, 108 mmol) in DME (700 mL) and stirred for 30 min. Ethyl formate (44 mL, 540 mmol) was added and the mixture was stirred overnight (in case of incomplete reaction, additional sodium ethoxide can be added and the reaction monitored by LC/MS). After the reaction was complete, the mixture was diluted with water (40 mL) and acidified to neutral pH with 1M HCl. The solid was filtered, washed with water and dried to afford 7-benzyloxy-6-methoxyquinolin-4-ol (22 g, 72%). 1H NMR (400 MHz, CDCl3): δ 10.7 (br s, 1H), 7.70 (s, 1H), 7.49-7.46 (t, 1H), 7.43-7.41 (br d, 2H), 7.37-7.33 (t, 2H), 7.30-7.28 (d, 1H), 6.84 (s, 1H), 6.21-6.19 (d, 1H), 5.21 (s, 2H), 3.96 (s, 3H). LC/MS (M+H=282).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08476298B2 |
|---|
| 出典データセット | uspto-grants-2013_07 |
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| ORD ID | ord-10a4f52c565f43579cabea06b2d425bb |
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| 出典メモ | uspto-grants-2013_07 |
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