Sodium Hydroxide → HCID 58476198, compound

HRID 1801394Notes

Reaction equation

HRID 1801394 reaction equation
[CH3:1][C:2]1([CH3:31])[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][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1([CH3:31])[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][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442263HCID 67442263, compound

Product 1

HCID 58476198HCID 58476198, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3,3-dimethyl-2-(2-(picolinamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (44 mg, 0.1 mmol, 1.0 eq.) and 1.3 mL aqueous solution of sodium hydroxide (2 M, 2.6 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 30 mg of 3,3-dimethyl-2-(2-(picolinamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; yield: 65%. MS (ESI+APCI) M+1=402.

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-7d6f8a6c27e848168b1dcfb8bc8b1eb6
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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