N-bromobutanimide → HCID 74892031, compound

HRID 2402385Notes

Reaction equation

HRID 2402385 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[Br:13]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[C:3]([Br:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 74892031HCID 74892031, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a flask was added 6-amino-3,4-dihydro-1(2H)-naphthalenone (5.30 g, 32.9 mmol) and DCM (329 mL) and the mixture was cooled to 0° C. N-bromosuccinimide (5.85 g, 32.9 mmol) was added portionwise over 1 hour. The mixture then was stirred at 0° C. for 3 hours. The reaction was quenched with aqueous sodium bicarbonate (100 mL) and then extracted with DCM (3×100 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The product was purified by silica gel chromatography using a gradient solvent system of 0-65% EtOAc/Hexanes. Concentration of the product-containing fractions yielded 6-amino-5-bromo-3,4-dihydronaphthalen-1(2H)-one (7.8 g, 87%) as a light tan solid. MS ESI calcd for C10H10BrNO 240 [M+H]+. found 240.

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate (100 mL)
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-39591ef096b84d11a9772af3c4554819
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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