4-Fluorophenylhydrazine hydrochloride → 7,8-Dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-[(4-fluorophenyl)hydrazone]

HRID 2425862ノート

反応式

HRID 2425862 の反応式
[N:1]1[C:11]2[C:10](=O)[CH2:9][CH2:8][C:7](=[O:13])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[F:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+].[K+].[Br-]>C(O)(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][N:23]=[C:10]2[CH2:9][CH2:8][C:7](=[O:13])[NH:6][C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:11]2=3)=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 253877Potassium BromideHCID 517045Sodium Acetate2 回HCID 457893917,8-Dihydro-5H-pyrido[3,2-B]azepine-6,9-dione

生成物 1

HCID 1363439307,8-Dihydro-5H-pyrido[3,2-b]azepine-6,9-dione 9-[(4-fluorophenyl)hydrazone]

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

183 mg (1.04 mmol) 5H-Pyrido[3,2-b]azepine-6,9(7H,8H)-dione and 186 mg (1.14 mmol) (4-fluorophenyl)hydrazine hydrochloride, and 90 mg (1.1 mmol) sodium acetate were suspended in glacial acetic acid (11 ml) and stirred for 1 hour at 70° C. After cooling to room temperature, the mixture was poured into a 5% aqueous sodium acetate solution. The mixture was extracted with 4×20 ml ethyl acetate. The combined organic layers were dried over sodium sulfate, and evaporated to dryness. Recrystallization from ethanol afforded a yellow solid. Yield: 170 mg (58%);m.p. 232-233° C.; IR (KBr): 3286 cm−1 (NH), 3119/3061 cm−1 (CH-arom.) 2956/2888 cm−1 (CH-aliph.), 1674 cm−1 (C═O); 1H-NMR (DMSO-d6, 400 MHz): δ (ppm)=2.54-2.58 (m, 2H, part of AA′XX′-system, azepine-CH2), 3.01-3.04 (m, 2H, part of AA′XX′-system, azepine-CH2), 7.03-7.07 (m, 2H, arom. H), 7.16-7.20 (m, 2H, arom. H), 7.33-7.40 (m, 2H, arom. H), 8.40 (dd, 1H, 4.4/1.6 Hz, arom. H), 9.35 (s, 1H, NH), 9.77 (s, 1H, NH); C15H13FN4O (284.30).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with 4×20 ml ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated to dryness
  5. customRecrystallization from ethanol
  6. customafforded a yellow solid

出典と根拠

ORDレコード
ord-12af29637751424dad40c4131d5a5bed
出典データセット
uspto-grants-2011_06
特許番号
US07968535B2

反応ノート

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