Acetic Anhydride → n-[2-(3,4-Dihydro-2h-4-chromenyl)ethyl]acetamide

HRID 428175Notes

Reaction equation

HRID 428175 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]#[N:13])[CH2:3][CH2:2]1.[C:14](OC(=O)C)(=[O:16])[CH3:15].C([O-])(=O)C.[Na+]>[Ni]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 133627812-(Chroman-4-yl)acetonitrile

Product 1

HCID 18177447n-[2-(3,4-Dihydro-2h-4-chromenyl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
50 °C

Procedure

The saturated cyano compound obtained in Step B is solubilized in the reactor of a Parr apparatus with acetic anhydride. Sodium acetate (1.5 eq.) and also Raney nickel (6 mg per 50 mg of product) are then introduced into the reaction medium. The whole is heated at 50° C. under hydrogen pressure of 40 psi for 12 hours. Once the solvent has been removed after returning to normal temperature and pressure conditions, extraction is carried out with ethyl acetate. Purification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3) results in the desired amide. Colourless gum.

Workup

  1. customOnce the solvent has been removed
  2. extractionafter returning to normal temperature and pressure conditions, extraction
  3. customPurification of the concentrated organic phase by flash chromatography (CHCl3/AcOEt 7/3)

Sources & evidence

ORD record
ord-c82db8a0e861465ab0d824918a33f986
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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