Potassium Hydroxide → HCID 9798607, compound

HRID 365539Notes

Reaction equation

HRID 365539 reaction equation
C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:26])([CH3:25])[CH2:17][CH2:18][N:19]3[CH:22]([CH3:24])[CH3:23])=[CH:14][C:13]=2[CH3:27])=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[CH:22]([N:19]1[C:20]2[C:15](=[CH:14][C:13]([CH3:27])=[C:12]([NH:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:28])=[O:3])=[CH:10][CH:9]=3)[CH:21]=2)[C:16]([CH3:26])([CH3:25])[CH2:17][CH2:18]1)([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 9951833HCID 9951833, compound2×

Product 1

HCID 9798607HCID 9798607, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-7-ylamino)-benzoic acid ethyl ester (Compound 46, 10.5 mg, 0.0275 mmol) in ethanol (1 mL) was treated with 2N KOH (0.5 mL) and stirred at 50° C. for 18 hours. 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=0.10) to give the title compound (9.3 mg, 96%) as a white solid: 1H NMR (300 MHz, CDCl3): δ1.17 (d, 6 H, J=6.6 Hz), 1.29 (s, 6 H), 1.72 (t, 2 H, J=6.0 Hz), 2.12 (s, 3 H), 3.15 (t, 2 H, J=6.0 Hz), 3.98 (sp, 1 H, J=6.6 Hz), 5.72 (br s, 1 H), 6.62 (s, 1 H), 6.79 (d, 2 H, J=8.7 Hz), 7.05 (s, 1 H), 7.96 (d, 2 H, J=8.7 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=0.10)

Sources & evidence

ORD record
ord-983503985faa42afbcf520c3976464f6
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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