Acetic Acid → 6-Bromo-3,4-dihydronaphthalene-1-carboxamide

HRID 63616

反応式

HRID 63616 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.[Si]([C:17]#[N:18])(C)(C)C.[OH:19]S(O)(=O)=O.CC(O)=O>C1(C)C=CC=CC=1.[Zn+2].[I-].[I-].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:17]([NH2:18])=[O:19])=[CH:7][CH2:6][CH2:5]2

参加物

8

反応物 4

HCID 176Acetic AcidHCID 1118Sulfuric Acid2 回HCID 82115Trimethylsilyl cyanideHCID 101050696-Bromo-1-tetralone

生成物 1

HCID 1185983436-Bromo-3,4-dihydronaphthalene-1-carboxamide収率 80%

試薬・触媒・溶媒 3

HCID 9883512zinc(II)iodide触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (5.46 g, 24.3 mmol) and ZnI2 (50 mg) in toluene (50 mL) was added TMSCN (4.82 mL, 48.6 mmol), and the solution stirred at 60° C. overnight. The reaction was cooled to rt, and H2SO4 (5.6 mL) was added. Then AcOH (34 mL), H2SO4 (25 mL) and H2O (4 mL) were added to the reaction, and it was heated to 105° C. for 3 h. The mixture was cooled and poured over ice-water (250 mL). The precipitate was collected by filtration, washed with water, and dried under vacuum to give 4.88 g (80%) of the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 2.25-2.33 (2H, m), 2.72 (2H, t, J=8.0 Hz), 6.51 (1H, t, J=4.6 Hz), 7.20 (1H, br s), 7.35-7.40 (3H, m), 7.65 (1H, br s). [M+H] calc'd for C11H10BrNO, 252, 254. found 252, 254.

後処理

  1. temperatureThe reaction was cooled to rt
  2. temperaturewas heated to 105° C. for 3 h
  3. temperatureThe mixture was cooled
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-6bb6bfdcada2480cbbd54a1d34aaccd8
出典データセット
uspto-grants-2016_09
特許番号
US09447046B2

関連ノート

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