Ethanol → HCID 66560939, compound

HRID 1910048Notes

Reaction equation

HRID 1910048 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:16])[CH2:14]Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])(=[O:19])C.[Na+].CCO.[OH-].[Na+]>O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:16])[CH2:14][OH:19])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 197113291-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

Product 1

HCID 66560939HCID 66560939, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solid mixture of 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone (1.0 g, 3.54 mmol) and sodium acetate (1.45 g, 17.71 mmol, 5 equiv) in a 40 mL vial was added EtOH (8 mL) and water (8 mL). The resulting suspension was heated in an oil bath at 70° C. for 3.5 hours. The mixture was cooled in an ice bath, to which was added 0.7 mL of 6 N NaOH. After 2 h, the cold mixture was quenched with 2 ml of 1N HCl, and then concentrated in vacuo. The residue was partitioned between 10% MeOH in DCM and water. The organic was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was taken up between DCM and ether to give a suspension, which was filtered. The yellow solids collected were washed with ether and dried under vacuum to give 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-hydroxyethanone (534 mg) as a light yellowish solid, which was used without further purification.

Workup

  1. temperatureThe mixture was cooled in an ice bath, to which
  2. customthe cold mixture was quenched with 2 ml of 1N HCl
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between 10% MeOH in DCM and water
  5. dry with materialThe organic was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a suspension, which
  9. filtrationwas filtered
  10. customThe yellow solids collected
  11. washwere washed with ether
  12. customdried under vacuum

Sources & evidence

ORD record
ord-a5d0dd1440cb475ba0f19a6767b1b4c9
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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