Morpholine → 4-(2-Chloro-5-methyl-4-nitrophenyl)-morpholine

HRID 1991074Notes

Reaction equation

HRID 1991074 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1Cl.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(OCCOCC)C>CCOC(C)=O.CCO>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 12375Ethylene glycol diethyl etherHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzene

Product 1

HCID 586836844-(2-Chloro-5-methyl-4-nitrophenyl)-morpholineYield 54%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

1,2-Dichloro-4-methyl-5-nitrobenzene (R.J. De Lang, et al. Tetrahedron (1998), 54(12), 2953-2966.) (1 g; 4.8 mmol), morpholine (1 ml) and 1,2-diethoxyethane (1 ml) were heated in a microwave oven at 160° C. for 2 h. The reaction mixture was poured on water/2N HCl 10/1 (50 ml) and extracted with TBME three times. The combined organic phases were dried over Na2SO4, evaporated and recrystallised from hot TBME to yield the title compound as yellow crystals (670 mg; 54%).

Workup

  1. extractionextracted with TBME three times
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated
  4. customrecrystallised from hot TBME

Sources & evidence

ORD record
ord-92b2134c644d4dfa9b062d72ee4f11d2
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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