Sodium Hydroxide → HCID 67441858, compound

HRID 1801302Notes

Reaction equation

HRID 1801302 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:8]=[C:9]([CH:13]3[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:25]([O:27]C)=[O:26])[CH:19]=4)[NH:14]3)[CH:10]=[CH:11][CH:12]=2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[CH:1]1([C:4]([NH:6][C:7]2[CH:8]=[C:9]([CH:13]3[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=4)[NH:14]3)[CH:10]=[CH:11][CH:12]=2)=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67442007HCID 67442007, compound

Product 1

HCID 67441858HCID 67441858, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

In a round bottom flask, to a mixture of methyl 2-(3-(cyclopropane-carboxamido) phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (109 mg, 0.29 mmol) in methanol (5 mL) and water (2.5 mL) was added a solution of sodium hydroxide (196 mg, 4.90 mmol) in water (2.5 mL). The resultant mixture was heated for reflux for 1.5 hours. 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 (silica gel, petroleum ether/ethyl acetate=3:1) to afford 2-(3-(cyclopropanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a solid product. (61 mg, yield: 58.2%). MS (ESI+APCI) M+1=347.2.

Workup

  1. temperaturefor reflux for 1.5 hours
  2. customThe methanol was removed under vacuum
  3. filtrationThe precipitates were collected by filtration
  4. custompurified by preparative Thin layer chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-da27a354f17d43e091aa61c7e5e5d11c
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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