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

HRID 505357Notes

Reaction equation

HRID 505357 reaction equation
[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

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 11459077HCID 11459077, compound

Product 1

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

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e992df891e934afd90911592033ae6e4
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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