Potassium Hydroxide → HCID 9952547, compound

HRID 365541Notes

Reaction equation

HRID 365541 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:15]2[CH:24]=[C:23]3[C:18]([C:19]([CH3:29])([CH3:28])[CH2:20][CH2:21][N:22]3[CH:25]([CH3:27])[CH3:26])=[CH:17][C:16]=2[CH3:30])[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[CH:25]([N:22]1[C:23]2[C:18](=[CH:17][C:16]([CH3:30])=[C:15]([N:11]([CH2:12][CH2:13][CH3:14])[C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:31])=[O:3])=[CH:10][CH:9]=3)[CH:24]=2)[C:19]([CH3:29])([CH3:28])[CH2:20][CH2:21]1)([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9888509HCID 9888509, compound2×

Product 1

HCID 9952547HCID 9952547, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution 4-[(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-propyl-amino]-benzoic acid ethyl ester (Compound 49, 12.0 mg, 0.0284 mmol) in ethanol (1 mL) was treated with 2N KOH (0.5 mL) and stirred at 50° C. for 2 days. The solvent was removed under reduced pressure and the residue was washed with ethyl acetate and acidified with 2N HCl. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexane, Rf=0.28) to give the title compound (11 mg, 98%) as a white solid: 1H NMR (300 MHz, CDCl3): δ0.95 (t, 3 H, J=7.4 Hz), 1.16 (d, 6 H, J=6.6 Hz), 1.31 (s, 6 H), 1.69-1.80 (m, 4 H), 1.95 (s, 3 H), 3.15 (t, 2 H, J=5.9 Hz), 3.54 (br s, 2 H), 3.97 (sp, 1 H, J=6.6 Hz), 6.47 (d, 2 H, J=8.9 Hz), 7.08 (s, 1 H), 7.88 (d, 2 H, J=8.9 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (30% ethyl acetate in hexane, Rf=0.28)

Sources & evidence

ORD record
ord-afc8840cb891486abe6a2cfd4733c1f8
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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