Hydrochloric Acid → HCID 59599515, compound

HRID 2267009Notes

Reaction equation

HRID 2267009 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[CH:24]=[CH:23][C:13]([O:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#N)=[CH:17][N:16]=3)=[CH:12][CH:11]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-:31].[K+].C(O)(C)C.Cl.[OH2:38]>>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]([OH:38])=[O:31])=[CH:17][N:16]=3)=[CH:23][CH:24]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 59599579HCID 59599579, compound

Product 1

HCID 59599515HCID 59599515, compoundYield 17%

Conditions

Temperature
130 °C

Procedure

Mix 6-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenoxy]-nicotinonitrile (,0.14 g, 0.34 mmol), powdered potassium hydroxide (0.69 g, 12.20 mmol), isopropyl alcohol (1.5 mL) and water (1.5 mL). Heat to 130° C. for 8 hrs. Allow to cool to ambient temperature. Pour into water (20 mL) and acidify to pH 1 with hydrochloric acid (37% in water, 1 mL). Extract with ethyl acetate (3×30 mL). Combine the organic extracts, dry over magnesium sulfate, filter and concentrate under reduced pressure to obtain a residue. Purification using 5% isopropyl alcohol/chloroformchloroform to 10% isopropyl alcohol/chloroformchloroform as gradient eluent gives the title compound (0.02 g, 17%): MS (m/z): 420.1 (M−1). 1H NMR (acetone-d6) 12.94 (s, 1H), 8.77 (s, 1H), 8.40 (dd, J=2.4 Hz, 8.4 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 7.15 (d, J=8.4 Hz, 1H), 6.79 (d, J=9.2 Hz, 1H), 5.34 (s, 2H), 2.73 (t, J=7.5 Hz, 2H), 2.63 (s, 3H), 1.66-1.56 (m, 2H), 0.96 (t, J=7.5 Hz, 3H).

Workup

  1. temperatureAllow to cool to ambient temperature
  2. extractionExtract with ethyl acetate (3×30 mL)
  3. dry with materialCombine the organic extracts, dry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto obtain a residue
  7. customPurification

Sources & evidence

ORD record
ord-326d9b005f28479bbba037cffdf95a7f
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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