Sodium Hydroxide → HCID 53492381, compound

HRID 2045647Notes

Reaction equation

HRID 2045647 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]2[C:27]([CH3:29])([CH3:28])[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:30]([O:32]C)=[O:31])[CH:24]=3)[NH:19]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]2[C:27]([CH3:28])([CH3:29])[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:30]([OH:32])=[O:31])[CH:24]=3)[NH:19]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67440735HCID 67440735, compound

Product 1

HCID 53492381HCID 53492381, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(2-(3-fluorophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (1.99 g, 4.2 mmol, 1.0 eq.) in tetrahydrofuran/methanol (25 mL/25 mL) was added sodium hydroxide (24 mL, 22.63 mmol, 5.4 eq.). The mixture was heated to reflux and stirred for 5 h. LC-MS indicated that 2005467-032-01 was consumed. 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 1.357 g of 2-(2-(3-fluorophenylsulfonamido) phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as off-white solid. yield: 92.7% (for two steps). MS (ESI+APCI) M+1=455.2.

Workup

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

Sources & evidence

ORD record
ord-355c611dd0ea47b1bb70bc862a18249b
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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