Cyclopropylamine → HCID 10517385, compound

HRID 1635102Notes

Reaction equation

HRID 1635102 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH:5]1[C:10]2[C:11]3[C:22](=O)[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[O:13][C:14](=[O:15])[C:9]=2[CH:8]=[CH:7][CH:6]=1>C(Cl)(Cl)Cl>[CH:1]1([N:4]2[C:22]3[C:21]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12](=[O:13])[C:11]=3[C:10]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:14]2=[O:15])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 265728Indeno(1,2-c)isochromene-5,11-dione

Product 1

HCID 10517385HCID 10517385, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Cyclopropylamine (10 mL) was added to a stirred solution of benz[d]indeno[1,2-b]pyran-5,11-dione (2) (0.28 g, 1.1 mmol) in CHCl3 (10 mL). The red solution stirred overnight before CHCl3 (50 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 red solid (0.3 g, 91%): mp 206-208° C.; IR (thin film) 3751, 1665, 1500, 1420, 1311, 1083, 950 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.62 (d, 1H, J=7.7 Hz), 8.29 (d, 1H, J=8.4 Hz), 7.88 (d, 1H, J=7.0 Hz), 7.69 (td, 1H, J=6.9, 1.2 Hz), 7.59 (dd, 1H, J=6.1, 1.3 Hz), 7.40 (m, 3H), 3.37 (m, 1H), 1.45 (q, 2H, J=6.8 Hz), 0.99 (m, 2H); CIMS m/z (relative intensity) 288 (MH−, 100). Anal. Calcd for C19H13NO2: 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-ac90f3f5a5a94f6dbda54d0178f4650f
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

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