Dimethylamine → HCID 23153431, compound

HRID 492748Notes

Reaction equation

HRID 492748 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:18]([N:20]([CH2:23]C)[CH2:21]C)C.ClC(OC1C=CC=CC=1)=[O:27].CNC>O1CCCC1.CO>[N+:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:18](=[O:27])[N:20]([CH3:23])[CH3:21])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Product 1

HCID 23153431HCID 23153431, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-(4-nitrophenoxy)pyridine (761 mg) was dissolved in tetrahydrofuran (14 ml) under a nitrogen atmosphere, and then triethylamine (1.16 ml) and phenyl chloroformate (1.05 ml) were added dropwise while cooling in an ice water bath, followed by stirring for 30 min. To the reaction mixture was added 2 N dimethylamine (a solution in methanol) (6.95 ml), followed by stirring overnight. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:5). Fractions containing the target compound were concentrated under a reduced pressure to give a residue, which was then dried in vacuum to provide the titled compound (609 mg, 72.5%) as a brown solid.

Workup

  1. temperaturewhile cooling in an ice water bath
  2. stirringby stirring overnight
  3. customThe reaction mixture was partitioned between ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 to 1:5)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated under a reduced pressure
  11. customto give a residue, which
  12. customwas then dried in vacuum

Sources & evidence

ORD record
ord-48213f1c90814e329cff33c6786d968d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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