Sodium Hydroxide → HCID 67439955, compound

HRID 2045613Notes

Reaction equation

HRID 2045613 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]2[C:20]([CH3:22])([CH3:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:23]([O:25]C)=[O:24])[CH:17]=3)[NH:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]2[C:20]([CH3:22])([CH3:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:23]([OH:25])=[O:24])[CH:17]=3)[NH:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67441301HCID 67441301, compound

Product 1

HCID 67439955HCID 67439955, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of methyl 2-(3-acetamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (129 mg, 0.37 mmol) in methanol (10 mL) and water (5 mL) was added with a solution of sodium hydroxide (249 mg, 6.22 mmol) in water (5 mL). The resultant mixture was heated to 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-acetamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a solid. (41 mg, yield: 33.1%). MS (ES+APCI) M+1=339.1.

Workup

  1. temperatureto 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-5ac0a3828e364b288f5c62360037628c
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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