Sodium Hydroxide → HCID 58476236, compound

HRID 1801351Notes

Reaction equation

HRID 1801351 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[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)=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1>[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[C:22]([CH3:24])([CH3:23])[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)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441699HCID 67441699, compound

Product 1

HCID 58476236HCID 58476236, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(2-(cyclopropanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (57 mg, 0.15 mmol, 1.0 eq.) and 1.8 mL aqueous solution of sodium hydroxide (2 M, 3.76 mmol, 25 eq.) in tetrahydrofuran (3 mL) was stirred at reflux for 3 h. Thin layer chromatography indicated that the starting material was consumed completely. The tetrahydrofuran was removed under reduced pressure and the residue was acidified to pH 5-6 with 1 M hydrochloric acid. Then a lot of white precipitates were formed and collected by filtration to afford 47 mg of 2-(2-(cyclopropanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; yield: 86%. MS (ESI+APCI) M+1=365.

Workup

  1. temperatureat reflux for 3 h
  2. customwas consumed completely
  3. customThe tetrahydrofuran was removed under reduced pressure
  4. customThen a lot of white precipitates
  5. customwere formed
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a802ae1ac6e442308922447f0317cdd9
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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