Triethylamine → HCID 10591700, compound

HRID 1635103Notes

Reaction equation

HRID 1635103 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH2:13].[CH:15]1[C:20]2[C:21]3[C:32](=O)[C:31]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:22]=3[O:23][C:24](=[O:25])[C:19]=2[CH:18]=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[O:25]=[C:24]1[C:19]2[C:20](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:21]2[C:22](=[O:23])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[C:32]=2[N:13]1[CH2:12][C:11]([O:10][CH3:9])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 265728Indeno(1,2-c)isochromene-5,11-dione

Product 1

HCID 10591700HCID 10591700, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (2.7 mL, 19.4 mmol) was added to a stirred solution of glycine methyl ester hydrochloride (1.57 g, 12.5 mmol) in chloroform (30 mL). After 1 h, benz[d]indeno[1,2-b]pyran-5,11-dione (2) (1.24 g, 5.0 mmol) was added to the mixture. The red mixture stirred an additional 4 h before CHCl3 (100 mL) was added and the mixture washed with H2O (3×50 mL) and brine (1×50 mL), dried (MgSO4), and concentrated under reduced pressure to give an orange-red solid (1.48 g, 92%): mp 248-251° C.; IR (thin film) 2956, 1735, 1667, 1609, 1502, 1426, 1227, 981 cm−1; 1H NMR (CDCl3, 300 MHz) δ8.68 (d, 1H, J=8.0 Hz), 8.32 (d, 1H, J=8.2 Hz), 7.73 (td, 1H, J=7.1, 1.3 Hz), 7.61 (m, 1H), 7.47 (td, 1H, J=7.1, 1.1 Hz), 7.37 (m, 2H), 7.26 (m, 1H), 5.34 (s, 2H), 3.79 (s, 3H); CIMS m/z (relative intensity) 320 (MH+, 100). Anal. Calcd for C19H13NO4: C, H, N.

Workup

  1. additionwas added
  2. washthe mixture washed with H2O (3×50 mL) and brine (1×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12a2cee32bdb46d3981d5fc186447596
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

Loading…