Propylamine → 6-Propyl-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dione

HRID 1635101Notes

Reaction equation

HRID 1635101 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH:5]1[C:10]2[C:11]3[C:22](=[O:23])[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[O:13][C:14](=O)[C:9]=2[CH:8]=[CH:7][CH:6]=1>C(Cl)(Cl)Cl>[O:13]=[C:14]1[C:9]2[C:10](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11]2[C:22](=[O:23])[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:12]=2[N:4]1[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 265728Indeno(1,2-c)isochromene-5,11-dione

Product 1

HCID 3344736-Propyl-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dioneYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Propylamine (0.3 mL, 3 mmol) was added to a stirred solution of benz[d]indeno[1,2-b]pyran-5,11-dione (2) (0.49 g mmol) in CHCl3 (10 mL). The red solution stirred overnight before CHCl3 (75 mL) was added and the mixture washed with H2O (3×20 mL) and brine (1×20 mL), dried (MgSO4), and concentrated under reduced pressure to give a yellow-orange solid (0.32 g, 55%): mp 166-167° C.; IR (neat) 2967, 1660, 1502, 1427, 1317, 1193, 959 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.69 (d, 1H, J=8.0 Hz), 8.33 (d, 1H, J=9.0 Hz), 7.70 (td, 1H, J=9.0, 3.0 Hz), 7.62 (d, 1H, J=6.2 Hz), 7.40 (m, 4H), 4.46 (t, 2H, J=8.0 Hz), 1.92 (m, 2H), 1.12 (t, 3H, J=7.4 Hz); CIMS m/z (relative intensity) 290 (MH+, 100). Anal. Calcd for C19H15NO2: C, H, N.

Workup

  1. additionwas added
  2. washthe mixture washed with H2O (3×20 mL) and brine (1×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1182d131ecac4883a25c80960b28d932
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

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