Hydrochloric Acid → HCID 45256345, compound

HRID 2065664Notes

Reaction equation

HRID 2065664 reaction equation
[C:1]([CH:4]([NH:13][C:14]1[C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:27])[CH:20]=2)[N:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([OH:3])=[O:2].[H-].[Na+].Cl[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1.Cl>CN(C=O)C.O>[C:1]([CH:4]([NH:13][C:14]1[C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:27])[CH:20]=2)[N:15]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)=[CH:10][CH:11]=1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 67357599HCID 67357599, compound

Product 1

HCID 45256345HCID 45256345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-[1-carboxy-2-(4-hydroxy-phenyl)-ethylamino]-6-chloro-quinoline-3-carboxylic acid (114 mg, 0.294 mmol) (prepared according to the procedure described in Example 34), sodium hydride (60% oil dispersion; 65 mg, 1.44 mmol) and 2-chloroquinoline (118 mg, 0.72 mmol) in dry DMF (1 mL) is stirred for 40 h at 110° C. in closed reaction vial. After cooling, the reaction mixture is poured in water and acidified by aqueous HCl. Precipitate is filtered, washed with water, then with hexane. The residue is treated with methanol and filtered. Filtrate is concentrated under reduced pressure, water is added and the precipitate is recrystallized from a mixture of acetone-water, 4:1, to provide the title compound in low yield.

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. filtrationPrecipitate is filtered
  4. washwashed with water
  5. additionThe residue is treated with methanol
  6. filtrationfiltered
  7. concentrationFiltrate is concentrated under reduced pressure, water
  8. additionis added
  9. customthe precipitate is recrystallized from a mixture of acetone-water, 4:1

Sources & evidence

ORD record
ord-e8e5ff96c14b470ba3ddcdbcdc3b6705
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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