Sodium Hydroxide → HCID 58476209, compound

HRID 1801355Notes

Reaction equation

HRID 1801355 reaction equation
[CH:1]1([C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28]C)=[O:27])[CH:20]=3)[NH:15]2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1>[CH:1]1([C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]=3)[NH:15]2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442483HCID 67442483, compound

Product 1

HCID 58476209HCID 58476209, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(2-(cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (54 mg, 0.14 mmol, 1.0 eq.) and 1.8 mL aqueous solution of sodium hydroxide (2 M, 3.57 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 40 mg of 2-(2-(cyclobutanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; yield: 76%. MS (ESI+APCI) M+1=379.

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-3401ea344f264f2e938c46ad83a58400
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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