Hydrochloric Acid → HCID 66699577, compound

HRID 1818562Notes

Reaction equation

HRID 1818562 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:25]=[CH:24][C:13]([C:14]([C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])=[O:15])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].Cl>C(O)(=O)C.[Zn]>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:14]([OH:15])[C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH:23]=3)[C:21]#[N:22])=[CH:24][CH:25]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66699620HCID 66699620, compound

Product 1

HCID 66699577HCID 66699577, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Add zinc dust (5.00 g, 76.5 mmol) to a solution of 5-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-nicotinonitrile (4.50 g, 10.9 mmol) in acetic acid (70 ml) and stir vigorously. After 1 hour, cool reaction in an ice bath and add 1N hydrochloric acid (200 ml). Extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with acetone:hexanes to yield the title product as a white solid (2.80 g, 62%): 1H NMR (DMSO-d6) δ 0.86 (t, 3H), 1.47 (sextet, 2H), 2.56 (m, 5H), 5.22 (s, 2H), 5.88 (m, 1H), 6.32 (d, 1H), 6.71 (d, 1H), 7.44 (q, 4H), 7.79 (d, 1H), 8.27 (t, 1H), 8.88 (dd, 1H), 12.84 (s, 1H).

Workup

  1. temperaturecool
  2. customreaction in an ice bath
  3. extractionExtract with ethyl acetate
  4. dry with materialdry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue by flash chromatography
  9. washeluting with acetone

Sources & evidence

ORD record
ord-a1900fb1b4df412384cff5655247e85c
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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