Sodium Hydroxide → HCID 13579997, compound

HRID 482891Notes

Reaction equation

HRID 482891 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:15]=1)=[O:5])C.[OH-].[Na+]>CO>[CH3:16][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13579990HCID 13579990, compound

Product 1

HCID 13579997HCID 13579997, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid ethyl ester (1.6 g) in methanol (25 ml) is treated with N sodium hydroxide (8 ml) and heated at reflux temperature for 4 hours. The solution is concentrated, diluted with water and the solution is extracted with ethyl acetate. The washed extract is dried and evaporated to a viscous residue which crystallizes after trituration with ether. Recrystallization of the product (0.119 g) from methanol-ethyl acetate solution gives pure 5,6,7,8-tetrahydro-2-methyl-3-quinolinecarboxylic acid, m.p. 196° C.-197° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 4 hours
  3. concentrationThe solution is concentrated
  4. additiondiluted with water
  5. extractionthe solution is extracted with ethyl acetate
  6. extractionThe washed extract
  7. customis dried
  8. customevaporated to a viscous residue which
  9. customcrystallizes after trituration with ether
  10. customRecrystallization of the product (0.119 g) from methanol-ethyl acetate solution

Sources & evidence

ORD record
ord-1b7b329e2dad44b9bb0a5c47bfc8dd40
Source dataset
uspto-grants-1986_03
Patent number
US04576949

Reaction notes

Loading…