N-Boc-4-hydroxyaniline → Tert-butyl 4-(2-amino-3-nitropyridin-4-yloxy)phenylcarbamate

HRID 217793

反応式

HRID 217793 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[C:24]=1[N+:30]([O-:32])=[O:31]>CN(C=O)C.C(OCC)(=O)C>[NH2:29][C:25]1[C:24]([N+:30]([O-:32])=[O:31])=[C:23]([O:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=2)[CH:28]=[CH:27][N:26]=1

参加物

6

反応物 3

HCID 2756771N-Boc-4-hydroxyanilineHCID 40716944-Chloro-3-nitropyridin-2-amineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 42626044Tert-butyl 4-(2-amino-3-nitropyridin-4-yloxy)phenylcarbamate収率 66.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

Tert-butyl 4-hydroxyphenylcarbamate (3.63 g, 17.4 mmol) was dissolved in dry DMF (150 mL). Potassium tert-butoxide (2.62 g, 23.4 mmol) was added and the stirring was continued for 30 minutes at room temperature. 4-Chloro-3-nitropyridin-2-amine (3.0 g, 17.3 mmol) was added as a solid in one portion and the reaction mixture was subsequently heated at 85° C. for 4 hours. The reaction mixture was cooled, diluted with ethyl acetate (800 ml) and washed with water (1×800 ml) and brine (2×800 ml). The organic layer was dried with magnesium sulphate and evaporated. The crude was chromatographed over silica (eluant ethyl acetate:cyclohexane 1:2) to yield 4.0 g (63% yield) of tert-butyl 4-(2-amino-3-nitropyridin-4-yloxy)phenylcarbamate.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water (1×800 ml) and brine (2×800 ml)
  3. dry with materialThe organic layer was dried with magnesium sulphate
  4. customevaporated
  5. customThe crude was chromatographed over silica (eluant ethyl acetate:cyclohexane 1:2)

出典と根拠

ORDレコード
ord-6c1610a9e41443cfabb853775213c53b
出典データセット
uspto-grants-2012_06
特許番号
US08198279B2

関連ノート

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