Morpholine → [4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl ester

HRID 492750Notes

Reaction equation

HRID 492750 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.C(N(CC)CC)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].N1CCOCC1>O1CCCC1.C(OCC)C>[C:29]1([O:28][C:26](=[O:27])[NH:1][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=3)[CH:5]=[CH:4][N:3]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 229367164-(4-Nitrophenoxy)pyridin-2-amine

Product 1

HCID 57677544[4-(4-Nitrophenoxy)pyridin-2-yl]carbamic acid phenyl esterYield 93.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-(4-nitrophenoxy)pyridine (600 mg) was dissolved in tetrahydrofuran (12 ml) under a nitrogen atmosphere, and then triethylamine (1.09 ml) and phenyl chloroformate (0.979 ml) were added dropwise thereto, followed by stirring for 20 min. To the reaction mixture was added morpholine (1.81 ml), followed by stirring for 25 min. 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 suspended in diethyl ether. The solid was filtered off, and dried under aeration to provide the titled compound (854 mg, 93.8%) as a brown solid.

Workup

  1. stirringby stirring for 25 min
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order, and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customto give a residue, which
  7. filtrationThe solid was filtered off
  8. customdried under aeration

Sources & evidence

ORD record
ord-e434e20e2bc44b729cd41bb43e5c1f9d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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