Ethanol → HCID 68681861, compound

HRID 2265894Notes

Reaction equation

HRID 2265894 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:32])=[C:6]2[C:11]=1[CH:10]([C:12]([OH:14])=[O:13])[N:9]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:8][CH2:7]2.OS(O)(=O)=O.[CH2:38](O)[CH3:39]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:32])=[C:6]2[C:11]=1[CH:10]([C:12]([O:14][CH2:38][CH3:39])=[O:13])[N:9]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:22][CH:23]=1)(=[O:16])=[O:17])[CH2:8][CH2:7]2

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric Acid2×HCID 66879081HCID 66879081, compound

Product 1

HCID 68681861HCID 68681861, compound

Procedure

0.60 g (1.2 mmol) of 8-bromo-2-[4-(4-fluorophenoxy)benzenesulfonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (crude product, 21C) are mixed with 0.25 ml of conc. H2SO4 in 10 ml of ethanol and heated to reflux. After five hours, a further 0.25 ml of conc. H2SO4 is added, and heating to reflux is continued for one hour. For workup, the mixture is concentrated, and the residue is taken up in sat. Na2CO3 solution and extracted twice with dichloromethane. The organic phases are dried with MgSO4, and the solvent is removed in vacuo. The crude product obtained in this way can be reacted further without purification.

Workup

  1. temperatureheated to reflux
  2. temperatureheating
  3. temperatureto reflux
  4. waitis continued for one hour
  5. concentrationFor workup, the mixture is concentrated
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe organic phases are dried with MgSO4
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7d56bf58aede433fbea246c24fa9ce9a
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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