Nitric Acid → HCID 19045274、化合物

HRID 1781371ノート

反応式

HRID 1781371 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[N+:18]([O-])([OH:20])=[O:19].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 944Nitric Acid2 回HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 1233903N-methylspiro[2H-1-benzopyran-2,4'-piperidine]4(3H)-one

生成物 1

HCID 19045274HCID 19045274、化合物収率 77%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
0 °C

実験手順

Sulfuric acid (55 ml) was cooled to 0° C. and was stirred as 3,4-dihydro-1'-methyl-spiro[2H-1-benzopyran-2,4'-piperidin]-4-one (11.56 g, 0.05 mol) was added over 20 minutes. Some gum separated. A solution of 90% nitric acid (2.5 ml, 0.0525 mol) in sulfuric acid (5 ml) was added over 20 minutes. The mixture was stirred for 2 hours at 0° C. and then for 1 hour at room temperature. A solution resulted but nitration was not complete. 90% Nitric acid (0.3 ml, 0.007 mol) was added and stirring was continued for 1 1/2 hours at room temperature. The reaction solution was poured into a mixture of ice, ethyl acetate, and sodium bicarbonate (210 g). The basic mixture was filtered, the ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate (150 ml). The combined ethyl acetate extracts were washed with saturated NaCl, dried, filtered and concentrated in vacuo to yield 10.6 g (77%) of product

後処理

  1. additionwas added over 20 minutes
  2. customSome gum separated
  3. waitfor 1 hour at room temperature
  4. customA solution resulted
  5. stirringstirring
  6. customwas continued for 1 1/2 hours at room temperature
  7. filtrationThe basic mixture was filtered
  8. customthe ethyl acetate layer was separated
  9. extractionthe aqueous layer was extracted with ethyl acetate (150 ml)
  10. washThe combined ethyl acetate extracts were washed with saturated NaCl
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f5952f2d3c1a47b8a5eff37ecec2b712
出典データセット
uspto-grants-1997_05
特許番号
US05633247

反応ノート

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