Ethanol → 4-[(1-Isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydro-quinolin-6-yl)(cyclopropylmethyl)amino]benzoic acid

HRID 365524Notes

Reaction equation

HRID 365524 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:15]([C:20]3[CH:30]=[CH:29]C=C[C:21]=3[C:22](OCC)=O)[CH2:16][CH:17]3[CH2:19][CH2:18]3)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:32])([CH3:31])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[OH-:33].[K+].[CH2:35]([OH:37])[CH3:36]>>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:15]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[C:20]3[CH:30]=[CH:29][C:36]([C:35]([OH:33])=[O:37])=[CH:22][CH:21]=3)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:32])([CH3:31])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 53850501Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)(cyclopropylmethyl)amino]benzoate2×

Product 1

HCID 98014624-[(1-Isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydro-quinolin-6-yl)(cyclopropylmethyl)amino]benzoic acidYield 67%

Conditions

Temperature
40 °C

Procedure

4 Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)(cyclopropylmethyl)amino]benzoate (Compound 25, 0.1 g, 0.2 mmol) was dissolved in ethanol (4.0 mL) and the solution treated with 1.7 M KOH (1.0 mL). The solution was heated to 40° C. and stirred for 24 hours. The solution was cooled and concentrated under reduced pressure. The residue was diluted with water, acidified with 10% HCl, and extracted with ether (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. Purification by recrystallization in ethanol gave the title compound (63 mg, 67%).

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ether (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification
  10. customby recrystallization in ethanol

Sources & evidence

ORD record
ord-2504e6a8bdf24acdaecfc8f2c7ac0984
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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