Chlorosulfonic acid → 6-Bromoisoquinoline

Temperatur

45 °C

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.

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

ORD-Eintrag

ord-64832c05b3cc49e5ac0d766a34e2b5bc

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09334269B2