Sodium Hydroxide → HCID 67441013, compound

HRID 1801322Notes

Reaction equation

HRID 1801322 reaction equation
[CH3:1][C:2]1([CH3:32])[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:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1([CH3:32])[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:31])[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67441299HCID 67441299, compound

Product 1

HCID 67441013HCID 67441013, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of methyl 3,3-dimethyl-2-(3-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (139 mg, 0.32 mmol) in methanol (5 mL) and water (2.5 mL) was added a solution of sodium hydroxide (220 mg, 5.50 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. The precipitates were collected by filtration, purified by preparative thin layer chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to afford 3,3-dimethyl-2-(3-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a solid. (70 mg, yield: 52.2%). MS (ESI+APCI) M+1-OH=397.2.

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-e7bf3b7714e7461eaf0946ded6c802e8
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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