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

HRID 1245695노트

반응식

HRID 1245695 반응식
[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

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 219120471-Ethyl-propyl[6-methyl-3-nitro-2-(4-chloro-2,6-dimethyl-phenoxy)-pyridin-4-yl]-amine

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2e4e59706f1e429fb30b5903f78de05a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125880B1

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