Lithium Hydroxide → Quinoline

HRID 857279Notes

Reaction equation

HRID 857279 reaction equation
COC(=O)C1C=CC=C([C:10]2[CH:11]=[C:12](C(S(C)(=O)=O)(C)C)[CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)C=1.[Li+].[OH-]>C1COCC1.[OH-].[Na+]>[N:18]1[C:19]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68887704Methyl 3-{6-[1-methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}benzoate

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-[6-(1-methanesulfonyl-1-methylethyl)-quinolin-8-yl]-benzoic acid methyl ester from Step 1 (1.0 eq) in THF (20 mL) was added LiOH (2.5 eq; 2.0N in water). The mixture was stirred at 65° C. for 6 h then poured in NaOH (1N) then extracted with CH2Cl2 (2×). The organic extracts were discarded while the aqueous phase was acidified to pH=5 using AcOH. The latter was extracted with CH2Cl2 (5×). The combined organic extracts were dried over MgSO4, filtered and concentrated. The resulting solid was stirred in a mixture of EtOAc:Hex:Et2O (0.1:1:1) then filtered to afforded the title compound as a white solid.

Workup

  1. extractionthen extracted with CH2Cl2 (2×)
  2. extractionThe latter was extracted with CH2Cl2 (5×)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe resulting solid was stirred in a mixture of EtOAc
  7. filtrationHex:Et2O (0.1:1:1) then filtered

Sources & evidence

ORD record
ord-672c7d9d97bf47928e930b138b86898c
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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