Sodium Hydroxide → 2-(4-(Cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 2045635Notes

Reaction equation

HRID 2045635 reaction equation
[C:1]1([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[C:25]([CH3:27])([CH3:26])[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:28]([O:30]C)=[O:29])[CH:22]=4)[NH:17]3)=[CH:12][CH:11]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH:16]3[C:25]([CH3:27])([CH3:26])[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:28]([OH:30])=[O:29])[CH:22]=4)[NH:17]3)=[CH:14][CH:15]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67441989Methyl 2-(4-(cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 584761752-(4-(Cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of methyl 2-(4-(cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (217 mg, 0.52 mmol) in methanol (3 mL) and water (1.5 mL) was treated with a solution of sodium hydroxide (353 mg, 2.63 mmol) in water (1.5 mL) 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 2M hydrochloric acid to pH=1. The precipitates were collected by filtration to afford 100 mg of 2-(4-(cyclohex-1-enecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow solid Yield: 53%. MS (ESI+APCI) M+1=405.2.

Workup

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

Sources & evidence

ORD record
ord-ea00584e6b5d41b287c9f3272eed05f2
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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