Sodium Hydroxide → HCID 53492317, compound

HRID 1801278Notes

Reaction equation

HRID 1801278 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([O:27]C)=[O:26])[CH:19]=3)[NH:14]2)=[CH:9][CH:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>CO.O>[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[C:22]([CH3:23])([CH3:24])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=3)[NH:14]2)=[CH:11][CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67440443HCID 67440443, compound

Product 1

HCID 53492317HCID 53492317, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of methyl 2-(4-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (46 mg, 0.12 mmol) in methanol (3 mL) and water (1.5 mL) was added a solution of sodium hydroxide (82 mg, 2.06 mmol.) in water (1.5 mL). The resultant mixture was heated to reflux until the completion of the reaction (monitored by thin layer chromatography). Methanol was removed under vacuum. The residue was acidified with 2 M hydrochloric acid to pH=1. The precipitates were collected by filtration to afford 2-(4-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid, 40 mg, 92% yield; MS (ESI+APCI) M+1=367.6.

Workup

  1. temperatureto reflux until the completion of the reaction (monitored by thin layer chromatography)
  2. customMethanol was removed under vacuum
  3. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-be97d32ad4bf4388a10eb34d9812d0b2
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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