9-Methylacridine → 9-Bromomethylacridine

HRID 1774081Notes

Reaction equation

HRID 1774081 reaction equation
[CH3:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.C1C(=O)N([Br:23])C(=O)C1>ClCCl>[Br:23][CH2:1][C:2]1[C:15]2[C:10]([N:9]=[C:8]3[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]3)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 119139-MethylacridineHCID 67184N-bromobutanimide

Product 1

HCID 1509309-BromomethylacridineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-methylacridine (1.93 g, 10 mmol) in dichloromethane (100 mL) was added NBS (1.78 g, 10 mmol) portion-wise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1:5) as eluent to afford 10 (2.08 g) in 77% yield. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.8 Hz, 4H), 7.81 (t, J=8.0 Hz, 2H), 7.68 (t, J=8.0 Hz, 2H), 5.42 (s, 2H). 13C NMR (400 MHz, CDCl3) δ 148.9, 138.7, 130.5, 130.1, 126.8, 123.8, 123.4, 23.1. MS (FAB) m/z Calcd for C14H10BrN 272.1 Found 2722. [M]+.

Workup

  1. additionAfter complete addition
  2. washThe resulting solution was washed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-412ea6b0072f48fea62925b196fc61fa
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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