Water → HCID 9899728, compound

HRID 884417Notes

Reaction equation

HRID 884417 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH3:12][C@H:13]1[O:18][C@@H:17]([CH3:19])[CH2:16][NH:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:19][C@H:17]1[O:18][C@@H:13]([CH3:12])[CH2:14][N:15]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 9899728HCID 9899728, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (1.3 g, 7.0 mmol), cis-2,6-dimethylmorpholine (2.5 g, 20 mmol), and K2CO3 (3.0 g, 22 mmol) in DMF (20 mL) was stirred at 110° C. for 48 h. The reaction mixture was cooled to room temperature, poured into water (300 mL). The resulting crude yellow solid was collected by vacuum filtration, air dried, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 95/5 CHCl3/ether) to yield the product as a yellow solid (1.2 g, 68%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting crude yellow solid was collected by vacuum filtration, air
  3. customdried
  4. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 95/5 CHCl3/ether)

Sources & evidence

ORD record
ord-80efc17198fc4f17a6c05956fba152a1
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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