Lithium Hydroxide → HCID 10544360, compound

HRID 977175Notes

Reaction equation

HRID 977175 reaction equation
C[O:2][C:3]([CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[NH:10][C:9](=[O:18])[C:8]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[OH-].[Li+]>O1CCCC1>[C:3]([CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[NH:10][C:9](=[O:18])[C:8]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10617376HCID 10617376, compound

Product 1

HCID 10544360HCID 10544360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methoxycarbonylmethoxy-7-chloro-3-phenyl-2(1H)-quinolone (Example 14) (0.13 g) in 50 ml tetrahydrofuran was stirred at room temperature for 30 mins with lithium hydroxide (18.2ml, 0.5M solution). The solvent was removed in vacuo and the residue was dissolved in water and acidified to pH1 (1 N HCl). The precipitate was collected by filtration to give the title compound, 23 mg; mp 269°-272° C. (propan-2-ol then DMF-water); Found: C, 61.63; H, 3.61; N, 4.60.C17H12NO4Cl requires C, 61.92; H, 3.69; N, 4.25%. δ (360 MHz, DMSO-d6) 4.05 (2H, s, OCH2), 7.29 (1H, dd, J=2.7, 8.7 Hz, 6-H), 7.35-7.47 (6H, m, Ar +8-H), 8.07 (1H, d, J=8.7 Hz, 5-H), 11.68 (1H, s, NH). m/z (CI-) 328 (M-1).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0f08ccf7fb214602aafc29a71cdac78c
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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