Sodium Hydroxide → 7,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid

HRID 47362

Reaction equation

HRID 47362 reaction equation
C([O:3][C:4]([CH:6]1[CH:15]2[CH2:16][CH:17]=[CH:18][CH:14]2[C:13]2[C:12]([Cl:19])=[CH:11][C:10]([Cl:20])=[CH:9][C:8]=2[NH:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:20][C:10]1[CH:11]=[C:12]([Cl:19])[C:13]2[CH:14]3[CH:18]=[CH:17][CH2:16][CH:15]3[CH:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 98832257,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid ethyl ester

Product 1

HCID 29147727,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 was saponified with 1.0 ml sodium hydroxide solution (6N, water) in 20.0 ml ethanol. The ethanolic solution was concentrated to small volume on a rotary evaporator, the residue was taken up in water, reacted with 6N HCl and the aqueous solution extracted three times over ether. The organic phase was washed neutral with water, dried over magnesium sulphate and concentrated to a reduced volume on a rotary evaporator.

Workup

  1. concentrationThe ethanolic solution was concentrated to small volume on a rotary evaporator
  2. customreacted with 6N HCl
  3. extractionthe aqueous solution extracted three times over ether
  4. washThe organic phase was washed neutral with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to a reduced volume on a rotary evaporator

Sources & evidence

ORD record
ord-cf3b603d4cea4b518d3f7d1107febe51
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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