N-methyl-2-pyrrolidone → N-(2-Allyl-4-cyano-3-hydroxyphenyl)-2,2-dimethylpropionamide

HRID 751053Notes

Reaction equation

HRID 751053 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[CH:9][C:10]=1[C:11]#[N:12])C=C.CN1C(=O)[CH2:24][CH2:23][CH2:22]1>>[CH2:24]([C:6]1[C:5]([OH:4])=[C:10]([C:11]#[N:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH:23]=[CH2:22]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 59754230N-(3-Allyloxy-4-cyanophenyl)-2,2-dimethylpropionamide

Product 1

HCID 59754237N-(2-Allyl-4-cyano-3-hydroxyphenyl)-2,2-dimethylpropionamide

Procedure

A solution of compound 10C (1.5 g, 5.8 mmol) in NMP (7 mL) was heated to 220° C. for 3 h. After cooling to rt, the reaction mixture was poured into ice/water, and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The crude product was chromatographed (silica gel) eluting with 0% to 50% EtOAc/hexane to furnish the title compound (0.7 g).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined EtOAc extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was chromatographed (silica gel)
  6. washeluting with 0% to 50% EtOAc/hexane

Sources & evidence

ORD record
ord-5bc7cebb7eaa4b059a0a16d28b0686fe
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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