Sodium Hydroxide → HCID 58476280, compound

HRID 1801359Notes

Reaction equation

HRID 1801359 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[C:27]([CH3:29])([CH3:28])[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:30]([O:32]C)=[O:31])[CH:24]=2)[NH:19]1)(=[O:10])=[O:9].[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[C:27]([CH3:28])([CH3:29])[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:30]([OH:32])=[O:31])[CH:24]=2)[NH:19]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441028HCID 67441028, compound

Product 1

HCID 58476280HCID 58476280, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(2-(2-fluorophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (62 mg, 0.13 mmol, 1.0 eq.) and 1.4 mL aqueous solution of sodium hydroxide (2 M, 2.7 mmol, 20 eq.) in tetrahydrofuran (4 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-(2-fluorophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; yield: 79%. MS (ESI+APCI) M+1=455.

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-76ab7a2aa04c4c569f8e47d299ab6ca2
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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