3-{4-[(2-Butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol → 3-{4-[(5-Amino-2-butyl-1-benzofuran-3-yl)carbonyl]phenoxy}propan-1-ol

HRID 43297Notes

Reaction equation

HRID 43297 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:8]=2[C:9]=1[C:10]([C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=1)=[O:11])[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:7]2[O:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:9]([C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:21][CH:22]=3)=[O:11])[C:8]=2[CH:23]=1

Participants

4

Reactant 1

HCID 566497733-{4-[(2-Butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol

Product 1

HCID 566497743-{4-[(5-Amino-2-butyl-1-benzofuran-3-yl)carbonyl]phenoxy}propan-1-olYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

180 g (0.453 mol) of 3-{4-[(2-butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol (formula(II)) dissolved in 1800 ml of methanol are loaded in a glass Buchi autoclave. Subsequently 9 g of Pd/C 10% (50% H2O) are added and H2 is loaded at a pressure of 4 bars. The mixture is left under stirring maintaining the temperature below 40° C. Once the consumption of hydrogen is complete, the reaction is left under stirring for approximately one further hour until it reaches 25° C. The catalyst is filtered on a Celite panel and the alcoholic solution containing the product is concentrated to residue. The crude product is crystallised, recovering it with 400 ml of toluene and the product is dried under a vacuum at 40° C. for 6-7 hours. 151 g of the product in the title are obtained.

Workup

  1. waitThe mixture is left
  2. temperaturemaintaining the temperature below 40° C
  3. customOnce the consumption of hydrogen
  4. waitthe reaction is left
  5. stirringunder stirring for approximately one further hour until it
  6. customreaches 25° C
  7. filtrationThe catalyst is filtered on a Celite panel
  8. additionthe alcoholic solution containing the product
  9. concentrationis concentrated to residue
  10. customThe crude product is crystallised
  11. customrecovering it with 400 ml of toluene
  12. customthe product is dried under a vacuum at 40° C. for 6-7 hours

Sources & evidence

ORD record
ord-5bad59cdeded42a99b37f502ae6a65f7
Source dataset
uspto-grants-2013_09
Patent number
US08536350B2

Reaction notes

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