4-Methyl-3-nitroaniline → 2-chloro-N-(4-methyl-3-nitrophenyl)pyridine-4-carboxamide

HRID 2117340Notes

Reaction equation

HRID 2117340 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17].[Cl:19][C:20]1[CH:25]=[C:24]([C:26](Cl)=[O:27])[CH:23]=[CH:22][N:21]=1>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([CH3:8])=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[O:27])[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 83904-Methyl-3-nitroanilineHCID 8471TriethylamineHCID 28000032-Chloropyridine-4-carbonyl chloride

Product 1

HCID 220579422-chloro-N-(4-methyl-3-nitrophenyl)pyridine-4-carboxamideYield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (31.8 ml) was added to a stirred mixture of 4-methyl-3-nitroaniline (15.8 g), 2-chloropyridine-4-carbonyl chloride (20 g) and methylene chloride (1 liter) and the resultant mixture was stirred at ambient temperature for 16 hours. The precipitate was isolated, washed with a saturated aqueous sodium bicarbonate solution and with methylene chloride and dried under vacuum at 40° C. There was thus obtained 2-chloro-N-(4-methyl-3-nitrophenyl)pyridine-4-carboxamide (10.2 g). The organic filtrate was washed with a saturated aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residue was triturated under methylene chloride and the resultant solid was isolated and dried under vacuum at 40° C. There was thus obtained a second crop (8.13 g) of 2-chloro-N-(4-methyl-3-nitrophenyl)pyridine-4-carboxamide; NMR Spectrum: (DMSOd6) 2.48 (s, 3H), 7.51 (d, 1H), 7.86 (m, 1H), 7.96 (m, 2H), 8.49 (m, 1H), 8.64 (m, 1H), 10.85 (s, 1H); Mass Spectrum: M+H+ 292 and 294.

Workup

  1. customThe precipitate was isolated
  2. washwashed with a saturated aqueous sodium bicarbonate solution and with methylene chloride
  3. customdried under vacuum at 40° C
  4. washThe organic filtrate was washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated under methylene chloride
  8. customthe resultant solid was isolated
  9. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-93c5af3d04a844d892c81d0576bf0278
Source dataset
uspto-grants-2008_10
Patent number
US07442704B2

Reaction notes

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