Tetrahydrofuran → HCID 12080911, compound

HRID 2195582Notes

Reaction equation

HRID 2195582 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:10]=[C:11]([C:19]([O:21][CH3:22])=[O:20])[CH:12]=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:5]=1)([O-])=O.O1CCCC1.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[C:11]([CH:10]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 12080910HCID 12080910, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12080911HCID 12080911, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a 1 liter egg plant-shaped flask, 66.24 g (0.2 moles) of dimethyl 5-(4-nitrophenoxy)isophthalate of the first intermediate compound, 6.39 g of a 10% palladium-active charcoal, 440 ml of tetrahydrofuran and 220 ml of ethanol were placed, and the resultant mixture was stirred for 24 hours under the atmosphere of hydrogen. The reaction fluid was filtered with Celite, and the filtrate was concentrated under a reduced pressure. Hexane was added to the concentrated fluid, and formed precipitates were separated by filtration. The obtained white solid substance was dried at 50° C. for 1 day under a reduced pressure, and 55.96 g of the second intermediate compound was obtained (the yield: 93%).

Workup

  1. filtrationThe reaction fluid was filtered with Celite
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. additionHexane was added to the concentrated fluid
  4. customformed
  5. customprecipitates
  6. customwere separated by filtration
  7. customThe obtained white solid substance was dried at 50° C. for 1 day under a reduced pressure

Sources & evidence

ORD record
ord-4f809e7d2d154ceb93497f4784250744
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

Loading…