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

HRID 458520노트

반응식

HRID 458520 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 184425025,6-Dimethoxy-2,3-dihydrobenzofuran-2-carbonitrileHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 184425035,6-Dimethoxy-2,3-dihydrobenzofuran-2-ylmethylamine수율 22.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6e803b879abe489b838827e4e4862d23
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192946B2

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