Hydrochloric Acid → HCID 59599463, compound

HRID 2267010Notes

Reaction equation

HRID 2267010 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:28])[CH2:26][CH3:27])=[C:21]([OH:29])[C:20]=3[CH3:30])[CH:12]=2)=[N:6][CH:5]=1.[OH-].[Li+].O.Cl>O1CCCC1>[OH:29][C:21]1[C:20]([CH3:30])=[C:19]([CH:24]=[CH:23][C:22]=1[C:25](=[O:28])[CH2:26][CH3:27])[O:18][CH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59599487HCID 59599487, compound

Product 1

HCID 59599463HCID 59599463, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 6-[3-(3-hydroxy-2-methyl-4-propionyl-phenoxymethyl)-phenoxy]-nicotinic acid methyl ester (0.10 g, 0.24 mmol) in tetrahydrofuran (2 mL). Add lithium hydroxide (0.007 g, 0.29 mmol) and water (0.5 mL). Stir at ambient temperature for 2 hrs. Add 1 N hydrochloric acid (5 mL) and extract with ethyl acetate (3×10 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/chloroform as gradient eluent gives the title compound (0.06 g, 58%): MS (m/z): 406.1 (M−1). 1H NMR (acetone-d6) 13.00 (s, 1H), 8.76 (s, 1H), 8.40 (dd, J=1.7 Hz, 8.4 Hz, 1H), 7.86 (d, J=9.2 Hz, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.44 (d, J=7.6 Hz, 1H), 7.38 (s, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 6.76 (d, J=9.2 Hz, 1H), 5.36 (s, 2H), 3.09 (q, J=7.2 Hz, 2H), 2.14 (s, 3H), 1.20 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextract with ethyl acetate (3×10 mL)
  2. dry with materialCombine the organic extracts, dry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customto obtain a residue
  6. customPurification

Sources & evidence

ORD record
ord-3a6127d9e0694e6ea8b440fc90309fa2
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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