Sodium Hydroxide → 1-(4-Carboxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

HRID 435463Notes

Reaction equation

HRID 435463 reaction equation
C[O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:15](=[O:24])[CH:16]([CH3:23])[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])=[O:4].[OH-].[Na+]>CO>[C:19]([CH2:18][CH2:17][CH:16]([CH3:23])[C:15]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][CH2:14][CH:5]1[C:3]([OH:4])=[O:2])=[O:24])([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131928991-(4-Carbomethoxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester

Product 1

HCID 131929001-(4-Carboxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 1.5 g of 1-(4-carbomethoxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester in 13.5 ml of methanol is added 13.5 ml of N aqueous sodium hydroxide and the mixture is stirred at room temperature for 3 hours. It is concentrated at room temperature and reduced pressure, the aqueous solution filtered, cooled and acidified with concentrated hydrochloric acid. The mixture is extracted with methylene chloride, the extract dried, evaporated, the residue recrystallized from petroleum ether and triturated with diethyl ether, to yield the 1-(4-carboxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid melting at 117°-119°.

Workup

  1. concentrationIt is concentrated at room temperature
  2. filtrationreduced pressure, the aqueous solution filtered
  3. temperaturecooled
  4. extractionThe mixture is extracted with methylene chloride
  5. customthe extract dried
  6. customevaporated
  7. customthe residue recrystallized from petroleum ether
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-269bcd4f776f47b3b83022aa11985f06
Source dataset
uspto-grants-1983_08
Patent number
US04401818

Reaction notes

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