Chlorosulfonic acid → 6-Bromoisoquinoline

HRID 522850

Reaction equation

HRID 522850 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][CH2:8][CH:9](OC)OC)=[CH:4][CH:3]=1.ClS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:15]=[C:14]2[C:5](=[CH:4][CH:3]=1)[CH:6]=[N:7][CH:8]=[CH:9]2

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 516892Sodium BicarbonateHCID 59226241N-(4-Bromobenzyl)-2,2-dimethoxyethanamine

Product 1

HCID 3136816-Bromoisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

To a stirred solution of N-(4-bromobenzyl)-2,2-dimethoxyethanamine (10 g, 0.037 mol) in CH2Cl2 (100 mL) was added ClSO3H (21.3 g, 0.18 mol) at −20° C. dropwise. The resulting reaction mixture was allowed to stir at 45° C. for 10 h. The resulting reaction mixture was diluted with CH2Cl2 and ice cold H2O, then neutralized with aqueous NaHCO3. The organic layer was separated and aqueous layer extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated at reduced pressure to get crude 6-bromoisoquinoline, which was purified by silica gel chromatography eluting with 5-15% EtOAc-hexanes to afford 6-bromoisoquinoline (0.9 g, 12%) as yellow liquid.

Workup

  1. customThe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. customThe organic layer was separated
  4. extractionaqueous layer extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-64832c05b3cc49e5ac0d766a34e2b5bc
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Linked notes

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