Hydrochloric Acid → 8,3-methylenedioxy-11H-indeno[1,2-c]isoquinoli ne hydrochloride

HRID 505357ノート

反応式

HRID 505357 の反応式
[CH2:1]1[O:17][C:16]2[CH:15]=[CH:14][C:5]([CH2:6][NH:7][CH2:8][CH:9](OC)OC)=[CH:4][C:3]=2[O:2]1.[CH:18](=O)[C:19]1[CH:28]=[CH:27][C:24]([O:25][CH3:26])=[C:21]([O:22][CH3:23])[CH:20]=1.[ClH:30]>>[ClH:30].[CH3:23][O:22][C:21]1[C:24]([O:25][CH3:26])=[CH:27][C:28]2[CH2:19][C:18]3[C:14]4[C:5](=[CH:4][C:3]5[O:2][CH2:1][O:17][C:16]=5[CH:15]=4)[CH:6]=[N:7][C:8]=3[C:9]=2[CH:20]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 11459077HCID 11459077、化合物

生成物 1

HCID 111641868,3-methylenedioxy-11H-indeno[1,2-c]isoquinoli ne hydrochloride

反応条件

温度
100 °C

実験手順

Concentrated HCl (20 mL) was added to a mixture of (3,4-methylenedioxybenzyl)-(2,2-dimethoxyethyl)amine (12b, 1.79 g, 7.49 mmol) and veratraldehyde (10a, 3.04 g, 0.018 mol). The reaction mixture was stirred at 100° C. for 3 h. The reaction mixture was then cooled and washed with ether (50 mL×3). Then it was brought to a basic pH with NH4OH. The mixture was extracted with chloroform (50 mL×4), washed with water (100 mL), dried (Na2SO4) and concentrated. The residue was dissolved in an organic solvent (200 mL chloroform). The mixture was filtered and HCl (2 M in ether, 40 mL) was added to the filtrate. The yellow precipitate that formed (0.7649 g, 29%) was collected by filtration. An analytical sample was prepared by recrystallizing 0.3655 g from methanol (50 mL), mp 257-259° C. 1H NMR (300 MHz, TFA) δ 8.88 (s, 1H), 7.69 (s, 1H), 7.39 (s, 1H), 7.33 (s, 2H), 6.21 (s, 2H), 4.18 (s, 2H), 4.02 (s, 3H), 4.01 (s, 3H); low resolution ESIMS m/z (rel intensity) 322 (100, MH+); high resolution ESIMS m/z (rel intensity) 322.1084 (100, MH+) (calculated mass 322.1079); IR (KBr) 3435, 3043, 2966, 2841, 2648, 2027, 1623, 1589, 1494, 1470, 1458, 1419, 1379, 1323, 1291, 1275, 1256, 1220, 1198, 1147, 1122, 1092, 1035, 969, 935, 902, 872, 835, 818, 785, 762, 743, 572 cm−1. Anal. Calcd for C19H16NO4Cl(H2O)0.7: C, 61.61; H, 4.74; N, 3.78. Found: C, 61.40; H, 4.98; N, 3.75.

後処理

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with ether (50 mL×3)
  3. extractionThe mixture was extracted with chloroform (50 mL×4)
  4. washwashed with water (100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in an organic solvent (200 mL chloroform)
  8. filtrationThe mixture was filtered
  9. additionHCl (2 M in ether, 40 mL) was added to the filtrate
  10. customThe yellow precipitate that formed (0.7649 g, 29%)
  11. filtrationwas collected by filtration
  12. customAn analytical sample was prepared
  13. customby recrystallizing 0.3655 g from methanol (50 mL), mp 257-259° C

出典と根拠

ORDレコード
ord-e992df891e934afd90911592033ae6e4
出典データセット
uspto-grants-2010_08
特許番号
US07781445B2

反応ノート

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