2,4,6-Trimethylphenol → (1-Ethyl-propyl)-[6-methyl-3-nitro-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-amine

HRID 1760667Notes

Reaction equation

HRID 1760667 reaction equation
ClCC[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([NH:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:7]=[CH:6][N:5]=1.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[OH:28].[CH3:29]C(C)([O-])C.[K+]>C1COCC1>[CH2:17]([CH:14]([NH:13][C:8]1[CH:7]=[C:6]([CH3:29])[N:5]=[C:4]([O:28][C:21]2[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:20]=2[CH3:19])[C:9]=1[N+:10]([O-:12])=[O:11])[CH2:15][CH3:16])[CH3:18]

Participants

5

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 22596029(2-Chloroethyl-3-nitro-pyridin-4-yl)-(1-ethyl-propyl)amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 9841694(1-Ethyl-propyl)-[6-methyl-3-nitro-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-amineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2-chloroethyl-3-nitro-pyridin-4-yl)-(1-ethyl-propyl)amine (80 mg, 0.31 mmol) and 2,4,6-trimethylphenol (43 mg, 0.31 mmol) in 2 ml of dry THF was added potassium tert-butoxide (35 mg, 0.31 mmol) and the resulting mixture was stirred at rt overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a yellow solid. The solid was purified through silica gel column chromatography using 6:4 ratio of chloroform:hexane as eluent to give 91 mg (83%) of the title compound as yellow solid, mp 160-162° C. 1H NMR (CDCl3) δ 7.62 (d, 1H), 6.87 (s, 2H), 6.18 (s, 1H), 3.40 (m, 1H), 2.30 (s, 3H), 2.15 (s, 3H), 2.10 (s, 6H), 1.5-1.8 (m, 4H), 0.99 (t, 6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. customThe solid was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-b3c3dd40474a434582c62bf5d819d6fb
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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