Hydrochloric Acid → 2-Methyl-6-[3-(quinolin-2-ylmethoxy)-propoxymethyl]-benzoic Acid
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl.O>C(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[C:3]=1[C:4]([OH:6])=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Methyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)-propoxymethyl]-benzoate (3.3 g, 8.7 mmol, EXAMPLE 35a) is dissolved in ethanol (81 mL). 10 N NaOH (9 mL, 90 mmol) is added and the contents are heated to 90° C. overnight. The reaction is cooled to r.t., and the volume reduced under vacuum. 2 N HCl (45 mL, 90 mmol) is added, and the pH is adjusted to ˜4. The contents are poured into water (400 mL) and extracted with dichloromethane (3×200 mL). The organic layers are combined, washed with brine (2×300 mL), dried over MgSO4, filtered and reduced under vacuum to dryness. The crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.27 (d, 2H), 7.86 (d, 1H), 7.73 (dd, 1H), 7.60-7.50 (m, 2H), 7.26-7.11 (m, 3H), 5.01 (s, 2H), 4.70 (s, 2H), 3.84 (t, 2H), 3.73 (t, 2H), 2.50 (s, 3H), 1.89 (quintet, 2H). MS (ESI) 366 (M+H)+.
Workup
- temperatureThe reaction is cooled to r.t.
- extractionextracted with dichloromethane (3×200 mL)
- washwashed with brine (2×300 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe crude material is purified by flash chromatography (silica, 3% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-22250470c04842bfaed49f3db11401ae
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06635655B1
Reaction notes
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