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

HRID 1245695ノート

反応式

HRID 1245695 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒2 回HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e4e59706f1e429fb30b5903f78de05a
出典データセット
uspto-grants-2006_10
特許番号
US07125880B1

反応ノート

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