Ethylamine → 6-Ethyl-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dione

HRID 1635100Notes

Reaction equation

HRID 1635100 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH:4]1[C:9]2[C:10]3[C:21](=O)[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:11]=3[O:12][C:13](=[O:14])[C:8]=2[CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:11](=[O:12])[C:10]=2[C:9]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:13]1=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 265728Indeno(1,2-c)isochromene-5,11-dione

Product 1

HCID 3342486-Ethyl-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dioneYield 78.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Ethylamine (0.2 mL, 3 mmol) was added to a stirred solution of benz[d]indeno[1,2-b]pyran-5, 11-dione (2) (0.49 g, 2 mmol) in CHCl3 (10 mL). The bright orange mixture stirred overnight. To the reaction mixture CHCl3 (100 mL) was added and the mixture washed with H2O (3×25 mL) and brine (1×25 mL), dried (MgSO4), and concentrated under reduced pressure to give an orange-red solid (0.43 g, 75%): mp 188-189° C.; IR (thin film) 2986, 1690, 1656, 1611, 1549, 1503, 1430, 1320, 1197, 991 cm−1; 1H NMR (DMSO-d6, 300 MHz) δ8.66 (d, 1H, J=8.3 Hz), 8.32 (d, 1H, J=7.9 Hz), 7.69 (dt, 1H, J=8.4, 1.4 Hz), 7.60 (dd, 1H, J=8.0, 1.4 Hz), 7.52 (d, 1H, J=6.9 Hz), 7.40 (m, 3H), 4.56 (q, 2H, J=7.2 Hz), 1.53 (t, 3H, J=7.2 Hz); CIMS, m/z (relative intensity) 276 (MH+, 100). Anal. Calcd for C18H13NO2: C, H, N.

Workup

  1. washthe mixture washed with H2O (3×25 mL) and brine (1×25 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-694b3cf2c3f643f18272da57b3c340d4
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

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