Hydrochloric Acid → HCID 59316601, compound

HRID 1845925Notes

Reaction equation

HRID 1845925 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[O:18][CH3:19])[N:14]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:13](=[O:28])[CH2:12][CH2:11]3)=[CH:4][CH:3]=1.Cl.O1CCOCC1.C(#N)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[O:18][CH3:19])[N:14]([CH2:20][C:21]([OH:23])=[O:22])[C:13](=[O:28])[CH2:12][CH2:11]3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 18373917Acetonitrile--water (1/1)HCID 68590745HCID 68590745, compound

Product 1

HCID 59316601HCID 59316601, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the crude (tert-butyl 2-(6-(4-chlorophenyl)-7-methoxy-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate) form Example 4D was added 4N hydrochloric acid in 1,4-dioxane (10 mL, 40 mmol). The reaction mixture was stirred at room temperature for 4 hours, and concentrated under reduced pressure. A second portion of 4N hydrochloric acid in 1,4-dioxane (10 mL, 40 mmol) and anhydrous N,N-dimethylformamide (2 mL) were added, and the mixture stirred for another 13 hours. The solvent was removed under reduced pressure, and the crude reaction product subjected to reverse phase HPLC with a gradient of acetonitrile/water (2% to 98%) to afford 2-(6-(4-chlorophenyl)-7-methoxy-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid (95 mg, 0.27 mmol, 72%). LCMS mz 346.0 (M+H), 368.0 (M+Na), anal HPLC >98% in purity. 1H NMR (400 MHz; CDCl3) δ 7.42 (d, J=8.6 Hz, 2H); 7.36 (d, J=8.6 Hz, 2H); 7.11 (s, 1H); 6.48 (s, 1H); 4.75 (s, 2H); 3.79 (s, 3H); 2.93 (m, 2H); 2.75 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringthe mixture stirred for another 13 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe crude reaction product

Sources & evidence

ORD record
ord-81d685859d6a45f486909d718d46db45
Source dataset
uspto-grants-2015_02
Patent number
US08952007B2

Reaction notes

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