4-Methyl-3-nitroaniline → N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide

HRID 1357698Notes

Reaction equation

HRID 1357698 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].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:17]1[CH:23]=[CH:22][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:19][C:18]=1[N+:24]([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 83904-Methyl-3-nitroanilineHCID 8471TriethylamineHCID 220579723-Morpholinobenzoyl chloride

Product 1

HCID 22057949N-(3-nitro-4-methylphenyl)-3-morpholinobenzamideYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Morpholinobenzoyl chloride (6.22 g) was added to a solution of 4-methyl-3-nitroaniline (4.20 g) and triethylamine (11.0 ml) in methylene chloride (150 ml) at ambient temperature under argon. The reaction mixture was stirred for 18 hours then diluted to 250 ml with methylene chloride. The mixture was washed with water (3×150 ml) and saturated sodium bicarbonate solution (2×100 ml), dried and evaporated to give a dark brown oil. The oil was triturated with diethyl ether and the solid collected and dried to yield N-(4-methyl-3-nitrophenyl)-3-morpholinobenzamide (1.82g); NMR: (CDCl3) 2.53 (s, 3H), 3.22 (t, 4H), 3.83 (t, 4H), 7.06 (dd, 1H), 7.23 (d, 1H), 7.37 (m, 2H), 7.42 (d, 1H), 7.88 (dd, 1H), 7.97 (s, 1H), 8.21 (d, 1H); m/z 340 (MH+); m.p. 149-150° C.

Workup

  1. washThe mixture was washed with water (3×150 ml) and saturated sodium bicarbonate solution (2×100 ml)
  2. customdried
  3. customevaporated
  4. customto give a dark brown oil
  5. customThe oil was triturated with diethyl ether
  6. customthe solid collected
  7. customdried

Sources & evidence

ORD record
ord-b0ac659dcdb3485585065a65ac4afe75
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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