Water → HCID 57556189, compound

HRID 2074515Notes

Reaction equation

HRID 2074515 reaction equation
[Cl:1]N1C=C(Cl)CN(Cl)N1.CN(C)C=O.[Cl:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)[C:22]([CH:33](O)[CH3:34])=[CH:21]2.O>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)[C:22]([CH:33]([Cl:1])[CH3:34])=[CH:21]2

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 21613252HCID 21613252, compoundHCID 57556193HCID 57556193, compound

Product 1

HCID 57556189HCID 57556189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,3,5-Trichlorotriazine (94 mg, 510 μmol) was added to dimethylformamide (0.04 mL, 510 μmol) at 25° C. After the formation of a white solid (10 min), DCM (3 mL) was added, followed by 1-(8-chloro-2-(3-fluorophenyl)quinolin-3-yl)ethanol (140.0 mg, 464 μmol), made from procedure K. After the addition, the mixture was stirred at room temperature for 4 h. Water (10 mL) was added, and then diluted with DCM (10 mL), the organic phase was washed with 15 mL of a saturated solution of NaHCO3, followed by water and brine. The organic layers were dried and concentrated. Purification of the residue by flash chromatography over silica gel, using 10% hexane in EtOAc, gave 8-chloro-3-(1-chloroethyl)-2-(3-fluorophenyl)quinoline, Mass Spectrum (ESI) m/e=320.0 (M+1).

Workup

  1. additionAfter the addition
  2. washthe organic phase was washed with 15 mL of a saturated solution of NaHCO3
  3. customThe organic layers were dried
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography over silica gel

Sources & evidence

ORD record
ord-9a86b792ef7e45619389fa807d254328
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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