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

HRID 63616

반응식

HRID 63616 반응식
[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

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 1118Sulfuric Acid2회HCID 82115Trimethylsilyl cyanideHCID 101050696-Bromo-1-tetralone

생성물 1

HCID 1185983436-Bromo-3,4-dihydronaphthalene-1-carboxamide수율 80%

시약·촉매·용매 3

HCID 9883512zinc(II)iodide촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6bb6bfdcada2480cbbd54a1d34aaccd8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

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