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

HRID 1760667ノート

反応式

HRID 1760667 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b3c3dd40474a434582c62bf5d819d6fb
出典データセット
uspto-grants-2005_01
特許番号
US06844351B1

反応ノート

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