Carbon Tetrachloride → HCID 86658928, compound

HRID 68167Notes

Reaction equation

HRID 68167 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:21].C1COCC1.[F:30][C:31]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH3:44])=[C:37]2[C:32]=1[C:33](=[O:53])[C:34]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1)=[CH:35][NH:36]2.[C:54]([CH:57](O)[CH2:58][NH-:59])([OH:56])=[O:55]>O>[F:30][C:31]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH3:44])=[C:37]2[C:32]=1[C:33](=[O:53])[C:34]([C:45]1[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=1)=[CH:35][NH:36]2.[C:54]([CH:57]([Cl:21])[CH2:58][NH-:59])([OH:56])=[O:55]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86658929HCID 86658929, compound

Product 1

HCID 86658928HCID 86658928, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenyl phosphine (2.47 g, 9.8 mmol) and carbon tetrachloride (1.4 g, 9.1 mmol) were added to a THF solution (30 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline-2-carboxy-(2-hydroxyethyl)amide (3.0 g, 7.24 mmol) and heated under reflux for 2 hours. The mixture was cooled to room temperature, and water was then added thereto, followed by extraction with dichloromethane. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=100:0→20:1). The purified material was concentrated to dryness under reduced pressure, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxy-(2-chloroethyl)amide (1.8 g, yield: 58%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. extractionfollowed by extraction with dichloromethane
  4. washThe thus-obtained organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. concentrationThe purified material was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-70f76ad6b44b4f4ea6524a0d4bf013ad
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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