Sodium Hydroxide → 3,3-Dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801311Notes

Reaction equation

HRID 1801311 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][C:19]([NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:18][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][C:19]([NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67442532Methyl 3,3-dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 534923193,3-Dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of methyl 3,3-dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (90 mg, 0.21 mmol) in methanol (3 mL) and water (1.5 mL) was added a solution of sodium hydroxide (143 mg, 3.57 mmol.) in water (1.5 mL). The resultant mixture was heated to reflux until the completion of the reaction (monitored by Thin layer chromatography). The 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 3,3-dimethyl-2-(4-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid, 75 mg, Yield 85% MS (ESI+APCI) M+1=415.6.

Workup

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

Sources & evidence

ORD record
ord-829acc96f6354ec6871aa938eff00ec5
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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