Sodium Hydroxide → HCID 58476220, compound

HRID 2045649Notes

Reaction equation

HRID 2045649 reaction equation
[CH3:1][C:2]1([CH3:27])[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][S:23]([CH3:26])(=[O:25])=[O:24].[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:27])[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][S:23]([CH3:26])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442010HCID 67442010, compound

Product 1

HCID 58476220HCID 58476220, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3,3-dimethyl-2-(2-(methylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (1.475 g, 3.769 mmol) in tetrahydrofuran/methanol (30 mL/30 mL) was added sodium hydroxide (26.5 mL, 53.126 mmol, 14.1 eq.). The mixture was heated to reflux and stirred for 0.5 h. LC-MS indicated that the reaction was completed. The mixture was concentrated and the residue was dissolved in water. The aqueous layer was basified to pH=4 by 1M hydrochloric acid. The precipitation was filtered, washed with water and dried to give 1.45 g of 3,3-dimethyl-2-(2-(methylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as off-white solid, yield: 86.3% (for two steps). MS (ESI+APCI) M+1=375.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in water
  5. customThe precipitation
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-a4962775c9ce4d47a02f8b4dd9bac167
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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