Lithium Hydroxide → 3,4-dihydro-2-quinolone (DHQ) derivative, 10

HRID 1376141Notes

Reaction equation

HRID 1376141 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([NH:15][CH:16]1[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:26][C:27]([O:29]C)=[O:28])[C:17]1=[O:31])=[O:14])=[CH:7]2>O.C1COCC1>[C:27]([CH2:26][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][CH:16]([NH:15][C:13]([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([Cl:3])=[CH:12][CH:11]=3)=[O:14])[C:17]1=[O:31])([OH:29])=[O:28]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 101944715-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

Product 1

HCID 101266823,4-dihydro-2-quinolone (DHQ) derivative, 10Yield 115.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (91.5 g, 2.18 mmol) in H2O (2 mL) was added to a stirring solution of 5-chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Example 1; 557 mg, 1.09 mmol) in THF (11 mL) and the reaction was stirred for 3 h. The reaction was quenched by addition of 1M aqueous HCl (40 mL) and EtOAc (60 mL) and the organic layer was dried (MgSO4), filtered and evaporated. The resultant white foam was triturated with hot Et2O (20 mL) cooled, filtered, dried and collected by filtration to afford the title compound (500 mg, 92%) as a white solid.

Workup

  1. customThe reaction was quenched by addition of 1M aqueous HCl (40 mL) and EtOAc (60 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resultant white foam was triturated with hot Et2O (20 mL)
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-76be88ee4ffd47fc93f4fc250063254f
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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