Chlorosulfonic acid → 4-Chloro-1-oxo-1,2-dihydroisoquinoline-7-sulfonyl chloride

HRID 2289805

Reaction equation

HRID 2289805 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH:3]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 8246494-Chloro-1(2H)-isoquinolone

Product 1

HCID 166583514-Chloro-1-oxo-1,2-dihydroisoquinoline-7-sulfonyl chlorideYield 58.6%

Conditions

Temperature
100 °C

Procedure

LRMS 180, 182 (MH+), 359, 361, 363 (M2H+). ##STR108## 4-Chloro-1-(2H)-isoquinolone (20.62 g, 115 mmol) was added portionwise to stirred chlorosulphonic acid (61 mL, 918 mmol) at 0° C. The mixture was heated at 100° C. for 3.5 d and then cooled to room temperature. The reaction mixture was added in small portions onto ice-water [CAUTION] and the resulting precipitate was collected by filtration. The solid was washed with water, triturated with MeCN and then dried in vacuo to give 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinesulphonyl chloride (18.75 g, 67.4 mmol) as a cream solid.

Workup

  1. temperaturecooled to room temperature
  2. additionThe reaction mixture was added in small portions onto ice-water [CAUTION]
  3. filtrationthe resulting precipitate was collected by filtration
  4. washThe solid was washed with water
  5. customtriturated with MeCN
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6f42d5ca5ef6417b9c53208d9c8113a4
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Linked notes

Loading…