Nitrogen → 7-Bromo-isoquinoline-5-Sulfonic Acid

HRID 1672362Notes

Reaction equation

HRID 1672362 reaction equation
[OH:1][S:2]([OH:5])(=O)=[O:3].N#N.Cl.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][N:16]=[CH:17]2)=[CH:12][CH:11]=1>>[Br:9][C:10]1[CH:11]=[C:12]([S:2]([OH:5])(=[O:3])=[O:1])[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][C:18]=2[CH:19]=1

Participants

4

Reactant 3

HCID 947NitrogenHCID 1118Sulfuric Acid2×HCID 211924607-Bromoisoquinoline hydrochloride2×

Product 1

HCID 866107547-Bromo-isoquinoline-5-Sulfonic AcidYield 85.3%

Procedure

Add fuming H2SO4 (2,000 mL, 21.33 mol; 26-29.5% free SO3) to a 5-L round bottom flask, equipped with a mechanical stirrer, reflux condenser, N2 line, and thermometer. Cool the fuming H2SO4 to ˜10° C. with an ice/acetone bath, then add 7-bromoisoquinoline HCl (500.00 g, 2.04 mol) portion-wise, keeping the temperature of the reaction mixture below ˜15-20° C. Upon complete addition of 7-bromoisoquinoline HCl, heat the resulting reaction mixture at ˜100° C. overnight. Cool the reaction mixture to room temperature, then slowly pour into a stirring solution of ice H2O. Recover the resulting precipitate by vacuum filtration, washing with H2O, then Et2O, and dry under vacuum filtration, followed by drying in a drying oven under reduced pressure at ˜35° C. to afford the title compound (501.42 g, 85% yield) as an off-white solid: TOF-MS [ES+; m/z] 287.9331/287.9330.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. custombelow ˜15-20° C
  4. temperatureheat
  5. customthe resulting reaction mixture at ˜100° C. overnight
  6. customRecover the resulting precipitate
  7. filtrationby vacuum filtration
  8. washwashing with H2O
  9. dry with materialEt2O, and dry under vacuum filtration
  10. customby drying in a drying oven under reduced pressure at ˜35° C.

Sources & evidence

ORD record
ord-934667dd4bfd4c4cadaabd48967b7c9d
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

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