3-Chloroaniline → HCID 59813873, compound

HRID 1925359Notes

Reaction equation

HRID 1925359 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([C:18](Cl)=[O:19])=[CH:13][CH:12]=[CH:11]3)=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[Cl:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30]>C(Cl)Cl.C(Cl)(Cl)Cl.O>[Cl:26][C:27]1[CH:28]=[C:29]([NH:30][C:18]([C:14]2[C:15]3[C:10](=[CH:9][C:8]([O:7][C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[CH:17][CH:16]=3)[CH:11]=[CH:12][CH:13]=2)=[O:19])[CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 79323-ChloroanilineHCID 516892Sodium BicarbonateHCID 86608624HCID 86608624, compound

Product 1

HCID 59813873HCID 59813873, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

6-(Pyridin-4-yloxy)-1-naphthoyl chloride (50 mg, 0.18 mmol) was suspended in CH2Cl2 and solid NaHCO3 (excess) was added. The mixture was blanketed with nitrogen and 3-chloroaniline (18.6 μL, 0.18 mmol) was added and the reaction mixture stirred at RT for 1 h. The reaction mixture was diluted with CHCl3 and water (using heat to dissolve the solids) and the organic layer further washed with brine, dried with Na2SO4, filtered and concentrated in-vacuo. The residue was crystallized from CH2Cl2/hexanes to give the title compound as a brown solid. MS (ESI pos. ion) m/z: 375.1 (M+H). Calc'd for C22H15ClN2O2−374.82.

Workup

  1. additionwas added
  2. temperatureusing heat
  3. dissolutionto dissolve the solids) and the organic layer
  4. washfurther washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo
  8. customThe residue was crystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-5a7e97853066452ea0cbd81a5c27de6a
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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