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

HRID 1245695Notes

Reaction equation

HRID 1245695 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 219120471-Ethyl-propyl[6-methyl-3-nitro-2-(4-chloro-2,6-dimethyl-phenoxy)-pyridin-4-yl]-amine

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-2e4e59706f1e429fb30b5903f78de05a
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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