Sodium Hydroxide → HCID 67440927, compound

HRID 1801344Notes

Reaction equation

HRID 1801344 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23](=[O:32])[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:17]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1([CH3:33])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([OH:14])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23](=[O:32])[CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67442300HCID 67442300, compound

Product 1

HCID 67440927HCID 67440927, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of methyl 3,3-dimethyl-2-(3-(3-phenylpropanamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (222 mg, 0.50 mmol) in methanol (6 mL) and water (3 mL) was added a solution of sodium hydroxide (341 mg, 8.53 mmol) in water (3 mL). The resultant mixture was heated to reflux for 1 hour. The methanol was removed under vacuum. The residue was acidified with 2 M hydrochloric acid to pH=5-6. The precipitates were collected by filtration, purified by preparative Thin layer chromatography (petroleum ether/ethyl acetate=3:1) to afford 3,3-dimethyl-2-(3-(3-phenylpropanamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a solid. (134 mg, yield: 66.1%); MS (ES+APCI) M+1-water=411.1.

Workup

  1. temperatureto reflux for 1 hour
  2. customThe methanol was removed under vacuum
  3. filtrationThe precipitates were collected by filtration
  4. custompurified by preparative Thin layer chromatography (petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-2da9f9daa6ef43cdaa00acc2886d91c8
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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