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

HRID 594766Notes

Reaction equation

HRID 594766 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1c523a9d4fb54737942b9cd1e45415ab
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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