Hydrogen Bromide → N-(1-bromo-8-chloroisoquinolin-3-yl)acetamide

HRID 40661Notes

Reaction equation

HRID 40661 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]#[N:12])[C:3]=1[C:4]#[N:5].[BrH:13].C([O-])(O)=O.[Na+].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>C(O)(=O)C.ClCCl>[Br:13][C:4]1[C:3]2[C:6](=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])[CH:10]=[C:11]([NH:12][C:26](=[O:28])[CH3:27])[N:5]=1

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59636321HCID 59636321, compound

Product 1

HCID 59636331N-(1-bromo-8-chloroisoquinolin-3-yl)acetamideYield 51%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-6-(cyanomethyl)benzonitrile (3.12 g, 17.7 mmol) was added to a solution of HBr in acetic acid (20 mL) and stirred at room temperature overnight. The reaction mixture was added drop wise to a saturated solution of NaHCO3. The resulting precipitate was collected by filtration to give a yellow solid, which was stirred in dichloromethane (100 mL). Triethylamine (3.7 mL, 26.5 mmol) and acetyl chloride (1.9 mL, 26.7 mmol) were added and the reaction mixture was stirred overnight at room temperature. Solvents were evaporated and residue was triturated with water, then ether, to the title compound as a pale yellow solid (2.67 g, 8.91 mmol, 51%). 1H NMR (d6-DMSO, 400 MHz) δ 8.47 (s, 1H), 8.00 (dd, 1H, J=8.6, 1.3 Hz), 7.74-7.72 (m, 1H), 7.67-7.64 (m, 1H), 2.14 (s, 3H). LC-MS (1) Rt=2.05 min; m/z (ESI+) 299 (MH+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customto give a yellow solid, which
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. customSolvents were evaporated
  5. customresidue was triturated with water

Sources & evidence

ORD record
ord-b2a67c0c94ba49549b9870d23149cc25
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

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