Sulfuric Acid → 5-Bromo-1,3-dichloroisoquinoline

HRID 2090057Notes

Reaction equation

HRID 2090057 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.S(=O)(=O)(O)O.[Br:18]N1C(=O)CCC1=O>CC#N>[Br:18][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[C:4]([Cl:12])[N:3]=[C:2]2[Cl:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 2986251,3-Dichloroisoquinoline

Product 1

HCID 205790315-Bromo-1,3-dichloroisoquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,3-dichloroisoquinoline (1.0 g, 5.1 mmol) in CH3CN (25 mL) was added concentrated sulfuric acid (1.0 mL, 18 mmol), followed by N-bromosuccinimide (1.1 g, 6.1 mmol). The mixture was stirred at room temperature for 60 hours. The precipitate was collected by filtration, washed with water, then dried in air to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 8.35 (d, J=9.0 Hz, 1H), 8.09 (s, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.57 (t, J=8.0 Hz, 1H). LC6: 3.74 min. (M+H): 278.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried in air

Sources & evidence

ORD record
ord-562b6eda41a041f6b3d0e9dc14d4aff1
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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