Hydrochloric Acid → 5,6-Dimethoxy-2,3-dihydrobenzofuran-2-ylmethylamine

HRID 458520ノート

反応式

HRID 458520 の反応式
[CH3:1][O:2][C:3]1[C:4]([O:14][CH3:15])=[CH:5][C:6]2[O:10][CH:9]([C:11]#[N:12])[CH2:8][C:7]=2[CH:13]=1.Cl.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([O:14][CH3:15])=[CH:5][C:6]2[O:10][CH:9]([CH2:11][NH2:12])[CH2:8][C:7]=2[CH:13]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 184425025,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 184425035,6-Dimethoxy-2,3-dihydrobenzofuran-2-ylmethylamine収率 22.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

5,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrile (Method 16; 2.63 g, 12.94 mmol) was dissolved in ethanol (700 ml) and hydrochloric acid (conc, 2.3 ml) and Pd on charcoal (10%, 1 g) were added. The mixture was hydrogenated under 3.5 atmosphere of hydrogen at 72° C. for 3 days. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in water and washed once with diethyl ether. The pH of the aqueous phase was adjusted to 10–11 with NaOH(aq) and the resulting solution was extracted several times with diethyl ether, then with DCM. The organic layers were dried, filtered and evaporated under reduced pressure. The diethyl ether extraction gave 0.6 g (22%) of pure product and the DCM extraction gave 2.0 g (74%) of pure product. NMR (400 MHz) 2.80–2.87 (m, 3H), 3.21 (dd, 1H), 3.74 (s, 3H), 3.76 (s, 3H), 4.72–4.82 (m, 1H), 6.47 (s, 1H), 6.82 (s, 1H).

後処理

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washwashed once with diethyl ether
  5. extractionthe resulting solution was extracted several times with diethyl ether
  6. customThe organic layers were dried
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. extractionThe diethyl ether extraction

出典と根拠

ORDレコード
ord-6e803b879abe489b838827e4e4862d23
出典データセット
uspto-grants-2007_03
特許番号
US07192946B2

反応ノート

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