Sodium Hydroxide → HCID 19592965, compound

HRID 613491Notes

Reaction equation

HRID 613491 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([C:17]([O:19]CC)=[O:18])=[CH:12]2)=[O:5].[OH-].[Na+]>O1CCCC1>[C:17]([C:13]1[CH:14]=[N:15][C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:26])([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19592761HCID 19592761, compound

Product 1

HCID 19592965HCID 19592965, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (300 mg), 1N sodium hydroxide solution (1.95 ml) in tetrahydrofuran (10 ml) was stirred for 6 hours at 50° C. The mixture was concentrated in vacuo, and water was added to the residue. The solution was washed with diethyl ether, and the aqueous layer was adjusted to pH 3 with 1N hydrochloric acid. The resulting precipitate was collected by filtration and washed with water to give 3-carboxy-8-(2,6-dichlorobenzoylamino)quinoline (251.1 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo, and water
  2. additionwas added to the residue
  3. washThe solution was washed with diethyl ether
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-c3cece73dbf8433f9a0b5ae682c9fe73
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…