Acetic Acid → 2-(4-Chloro-2,6-dimethyl-phenoxy)N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine

HRID 1831650Notes

Reaction equation

HRID 1831650 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([CH3:25])[C:5]([O:6][C:7]2[C:12]([N+:13]([O-])=O)=[C:11]([NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:10]=[C:9]([CH3:22])[N:8]=2)=[C:4]([CH3:26])[CH:3]=1.CC(O)=O>[Fe].O>[Cl:1][C:2]1[CH:24]=[C:23]([CH3:25])[C:5]([O:6][C:7]2[C:12]([NH2:13])=[C:11]([NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:10]=[C:9]([CH3:22])[N:8]=2)=[C:4]([CH3:26])[CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21912047HCID 21912047, compound

Product 1

HCID 219120942-(4-Chloro-2,6-dimethyl-phenoxy)N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

A mixture of [2-(4-chloro-2,6-dimethyl-phenoxy)-6-methyl-3-nitro-pyridin-4-yl]-(1-ethyl-propyl)-amine (810 mg, 2.14 mmol) and iron (Fe) (594 mg, 10.72 mmol) in 96 ml of 1:1 of AcOH:H2O was heated at reflux for 2 hours. Additional Fe (600 mg) was added. The mixture was heated for an additional 1.5 hours. The reaction mixture was concentrated to dryness. The residue was quenched with water, basified to pH 9.0 and filtered through celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give the title compound as a yellow oil. The oil was purified through silica gel column chromatography using chloroform as eluent to give 570 mg of 2-(4-chloro-2,6-dimethyl-phenoxy)-N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine as a tan solid, mp 72–74° C. 1H NMR(CDCl3)δ 7.04(s,2H), 6.11(s,1H), 4.03(d,1H), 3.30(m,1H), 3.07(s,1H), 2.14(s,3H), 2.10(s,6H), 1.4–1.75(m,4H), 0.97(t,6H)ppm. The corresponding di-HCl salt was prepared as a white solid, mp 208–210° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was heated for an additional 1.5 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customThe residue was quenched with water
  5. filtrationfiltered through celite
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0dae1060cb483bb450a979ee346f6f
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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