Sodium Hydroxide → 6-[(Phenylsulfonyl)amino]-5-quinolinecarboxylic acid

HRID 1725880Notes

Reaction equation

HRID 1725880 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]=2[C:21]([O:23]C)=[O:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]=2[C:21]([OH:23])=[O:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68863977Methyl 6-[(phenylsulfonyl)amino]-5-quinolinecarboxylate

Product 1

HCID 688636536-[(Phenylsulfonyl)amino]-5-quinolinecarboxylic acidYield 14.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of Example 96C (0.073 g, 0.21 mmol) in methanol (4 mL) was treated with 2 mL conc. NaOH and heated to 70° C. for 18 hours. The mixture was concentrated, diluted with water, acidified to pH 5 with 1M HCl, and extracted with dichloromethane. The extract was dried (MgSO4), filtered, and concentrated to provide the desired product (0.010 g). MS (ESI(+)) m/e 329 (M+H)+; (ESI(−)) m/e 327 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.01 (dd, 1H), 8.97 (m, 1H), 8.30 (d, 1H), 7.92 (d, 1H), 7.74 (m, 5H), 7.54 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e424d44732ec40c0812720aedb136358
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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