Water → 2-fluorodibenzo[b,f][1,4]oxazepin-11(10H)-one

HRID 1946572ノート

反応式

HRID 1946572 の反応式
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:6]=1[C:7](OC)=[O:8].C[Al](C)C.C1(C)C=CC=CC=1.O>C(Cl)Cl>[F:15][C:12]1[CH:13]=[CH:14][C:5]2[O:4][C:3]3[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=3[NH:1][C:7](=[O:8])[C:6]=2[CH:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 1140TolueneHCID 16682925TrimethylaluminumHCID 59783706Methyl 2-(2-aminophenoxy)-5-fluorobenzoate

生成物 1

HCID 122595332-fluorodibenzo[b,f][1,4]oxazepin-11(10H)-one収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Title compound 19 (802 mg, 3.07 mmol) was dissolved in DCM (10 mL) and the mixture was cooled to 0° C. Trimethylaluminum 2M in toluene (1.8 mL, 3.69 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature. The mixture was then heated to 45° C. for 45 h. The mixture was cooled to room temperature for the slow addition of water. The solution was extracted with ethyl acetate then washed twice with HCl (10%), water and saturated solution of bicarbonate. The organic layer was then dried over sodium sulfate and concentrated in vacuo until the product precipitated. The solid was filtered and dried to afford title compound 20 (511 mg, 73%) as a white solid. LRMS (ESI): (calc) 229.05 (found) 230.1 (MS)+.

後処理

  1. temperatureto warm to room temperature
  2. temperatureThe mixture was then heated to 45° C. for 45 h
  3. extractionThe solution was extracted with ethyl acetate
  4. washthen washed twice with HCl (10%), water and saturated solution of bicarbonate
  5. dry with materialThe organic layer was then dried over sodium sulfate
  6. concentrationconcentrated in vacuo until the product
  7. customprecipitated
  8. filtrationThe solid was filtered
  9. customdried

出典と根拠

ORDレコード
ord-423e55a7e9144145abe17e4c9797a7d5
出典データセット
uspto-grants-2013_03
特許番号
US08399452B2

反応ノート

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