Nitric Acid → 8-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

HRID 1633722

反応式

HRID 1633722 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2.[N+:14]([O-])([OH:16])=[O:15].O>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:14]([O-:16])=[O:15])=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2

参加物

6

反応物 3

HCID 944Nitric AcidHCID 962WaterHCID 112753358-Methoxy-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 111720678-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 7918Acetic Anhydride溶媒

反応条件

温度
0 °C

実験手順

A solution of 8-methoxy-1-tetralone (2.26 g, 13 mmol) (prepared as described in Chatterjee, A. Tetrahedron, (1980), 36, 2513-2520) in acetic anhydride (11.5 mL) was cooled to 0° C., treated with a mixture of fuming nitric acid (0.90 mL) in acetic acid (0.70 mL) dropwise over 1 hour, stirred at 0° C. for 1.5 hours, treated with water (150 mL) and extracted with diethyl ether (300 mL). The diether ether layer was washed with water (150 mL), washed with sodium bicarbonate solution (3×), washed with brine, dried (MgSO4), filtered and concentrated. Purification of the residue on silica gel using a gradient of 2:1 and then 3:2 and finally 1:1 hexanes:ethyl acetate provided the desired product as the more polar isomer.

後処理

  1. extractionextracted with diethyl ether (300 mL)
  2. washThe diether ether layer was washed with water (150 mL)
  3. washwashed with sodium bicarbonate solution (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue on silica gel using a gradient of 2:1

出典と根拠

ORDレコード
ord-170144955c944271a0017f417eb4653c
出典データセット
uspto-grants-2003_01
特許番号
US06503935B1

関連ノート

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