Chlorosulfonic acid → HCID 86625162, compound

HRID 1663398Notes

Reaction equation

HRID 1663398 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:8]=[C:9]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])[CH:10]=[CH:11][C:12]=1[OH:13]>>[Br:6][C:7]1[C:12]([OH:13])=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=[C:9]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])[CH:8]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 674122614-(3-Bromo-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

Product 1

HCID 86625162HCID 86625162, compound

Procedure

To 47 ml of chlorosulfonic acid, cooled to −10° C. in a pressure vessel under a nitrogen atmosphere, was slowly added 4-(3-bromo-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (20.25 g). The mixture was allowed to reach room temperature. After stirring for 17 h, the mixture was poured onto 800 ml of crushed ice and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ethyl acetate. The solids were collected and dried in vacuo.

Workup

  1. customto reach room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate
  7. customThe solids were collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-dcb4c1ab9c094dea87e31bda2fe5d4dd
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

Loading…