Hydrochloric Acid → HCID 68512873, compound

HRID 384499Notes

Reaction equation

HRID 384499 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)[NH:4][C:3]=1[CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:27]=1.C1COCC1.[OH-].[K+].Cl>C(O)C>[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)[NH:4][C:3]=1[CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH:34]2[CH2:35][CH2:36][O:37][CH2:38][CH2:39]2)[CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 68510220HCID 68510220, compound

Product 1

HCID 68512873HCID 68512873, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To an ice-cold suspension of ethyl 3-methyl-4-oxo-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}-1,4-dihydroquinoline-6-benzoate (158 mg) in ethanol (5.0 mL)-THF (3.0 mL) was added dropwise a 4M aqueous potassium hydroxide solution (0.18 mL), and the mixture was stirred at 65° C. for 15 hours. The reaction mixture was ice-cooled, and adjusted to a pH of 7 by adding 1M hydrochloric acid. The resulting solid was collected by filtration, washed with water, and dried to obtain 3-methyl-4-oxo-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}-1,4-dihydroquinoline-6-benzoic acid (103 mg).

Workup

  1. temperaturecooled
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7f79e6cd64144a7983c27c9fecf7b26c
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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