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

HRID 1760667노트

반응식

HRID 1760667 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b3c3dd40474a434582c62bf5d819d6fb
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844351B1

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