Pyridine → N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide

HRID 1828726Notes

Reaction equation

HRID 1828726 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])[CH2:3][CH2:2]1.[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].N1C=CC=CC=1>C(Cl)Cl>[N+:24]([C:18]1[CH:19]=[C:20]([NH:21][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=2)[CH:22]=[CH:23][C:17]=1[CH3:16])([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 83904-Methyl-3-nitroanilineHCID 220579723-Morpholinobenzoyl chloride

Product 1

HCID 22057949N-(3-nitro-4-methylphenyl)-3-morpholinobenzamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-morpholinobenzoyl chloride (0.24 g) in methylene chloride (5 ml) was added to a stirred mixture of 4-methyl-3-nitroaniline (0.15 g), pyridine (0.24 ml) and methylene chloride (10 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution. The organic layer was dried (MgSO4) and evaporated. The residual solid was triturated under diethyl ether and the resultant solid was isolated and dried to give N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide (0.28 g); NMR Spectrum: (DMSOd6) 3.2 (t, 4H), 3.3 (s, 3H), 3.78 (t, 4H), 7.19 (s, 1H), 7.4 (m, 2H), 7.47 (d, 2H), 8.0 (d, 1H), 8.83 (s, 1H), 10.23 (s, 1H).

Workup

  1. washThe organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customThe residual solid was triturated under diethyl ether
  5. customthe resultant solid was isolated
  6. customdried

Sources & evidence

ORD record
ord-54cce2d3a3044bf3a06fe5b2184616f2
Source dataset
uspto-grants-2006_06
Patent number
US07060700B2

Reaction notes

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