Hydrochloric Acid → HCID 53373258, compound

HRID 1846168Notes

Reaction equation

HRID 1846168 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19]COC)[C:6]([OH:23])=[C:5]([O:24][CH3:25])[CH:4]=1.Cl.[NH4+].[OH-]>CO>[CH3:26][N:2]([CH3:1])[C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:6]([OH:23])=[C:5]([O:24][CH3:25])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 67328822HCID 67328822, compound

Product 1

HCID 53373258HCID 53373258, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution containing 6-(Dimethylamino)-4-methoxy-2-(10-(methoxymethoxy)decyl)pyridin-3-ol in 5 mL of methanol was added a drop of conc HCl. The reaction mixture was stirred at reflux for 2 h. A drop of conc NH4OH was added and the mixture was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (1×10 cm). Elution with 9:1 dichloromethane-methanol afforded the expected product as a yellowish oil: yield 7 mg (40%); silica gel TLC Rf 0.2 (9:1 dichloromethane-methanol); 1H NMR (methanol) δ 1.29 (br m, 12H), 1.49 (quint, 2H, J=6.8 Hz), 1.62 (quint, 2H, J=7.2 Hz), 2.66 (dd, 2H, J=7.6, 7.6 Hz), 3.00 (s, 6H), 3.49 (t, 2H, J=6.8 Hz), 3.90 (s, 3H) and 6.11 (s, 1H); 13C NMR (methanol) δ 25.50, 28.06, 29.08, 29.13, 29.14, 29.20, 29.28, 30.09, 32.22, 38.16, 38.16, 54.90, 61.57, 87.88, 132.75, 143.86, 154.04 and 157.27; mass spectrum (APCI), m/z (M+H)+325.2489 (C18H33N2O3 requires 325.2491).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationthe mixture was concentrated under diminished pressure
  3. customThe residue was purified by chromatography on a silica gel column (1×10 cm)
  4. washElution with 9:1 dichloromethane-methanol

Sources & evidence

ORD record
ord-5aebba1c119044ca9ed2c6c92d87089d
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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