Lithium Hydroxide → HCID 21082101, compound

HRID 346999Notes

Reaction equation

HRID 346999 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:37])([C:31]4[N:35]([CH3:36])[CH:34]=[N:33][CH:32]=4)[C:19]4[CH:30]=[CH:29][C:22]([C:23]([O:25]C(C)C)=[O:24])=[CH:21][CH:20]=4)[CH:16]=3)[N:11]([CH3:38])[C:10](=[O:39])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:37])([C:31]4[N:35]([CH3:36])[CH:34]=[N:33][CH:32]=4)[C:19]4[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:29][CH:30]=4)[CH:16]=3)[N:11]([CH3:38])[C:10](=[O:39])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 21082090HCID 21082090, compound

Product 1

HCID 21082101HCID 21082101, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-1-methylethyl 4-[[4(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzoate (described in Example B12) (0.00369 mol) and LiOH. H2O (0.00369 mol) in THF (15 ml) and H2O (8 ml) was stirred at room temperature for 72 hours, poured out into H2O and washed with EtOAc. The aqueous layer was evaporated, taken up in 2-propanone/H2O and acidified with HCl/diethyl ether. The aqueous layer was evaporated. A part of the residue (0.3 g) was taken up in EtOH/diethyl ether. The precipitate was filtered off and dried, yielding 0.2 g (71%) of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzoic acid, mp. >260° C.

Workup

  1. washwashed with EtOAc
  2. customThe aqueous layer was evaporated
  3. customThe aqueous layer was evaporated
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-19b9bda90f1d4000b1a87adbec6b97df
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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