3,4,5-Trimethoxybenzaldehyde → 2-Amino-3-cyano-4-(3,4,5-trimethoxyphenyl)-7-methyl-4H-pyrrolo[2,3-h]chromene

HRID 490827Notes

Reaction equation

HRID 490827 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[OH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][N:20]2[CH3:25].[C:26](#[N:30])[CH2:27][C:28]#[N:29].N1CCCCC1>C(O)C>[NH2:30][C:26]1[O:15][C:16]2[C:24]([CH:6]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=3)[C:27]=1[C:28]#[N:29])=[CH:23][CH:22]=[C:21]1[N:20]([CH3:25])[CH:19]=[CH:18][C:17]=21

Participants

6

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 8010MalononitrileHCID 8082PiperidineHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 103630372-Amino-3-cyano-4-(3,4,5-trimethoxyphenyl)-7-methyl-4H-pyrrolo[2,3-h]chromeneYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3,4,5-trimethoxybenzaldehyde (53 mg, 0.27 mmol), 4-hydroxy-1-methylindole (40 mg, 0.27 mmol) and malononitrile (18 mg, 0.27 mmol) in 1.5 mL of ethanol was added piperidine (0.01 ml, 0.1 mmol). The solution was stirred at room temperature overnight and precipitates were observed. The precipitates were collected by filtration and dried to yield 70 mg (66%) of title compound as white solids. 1H NMR (CDCl3): 7.06-7.02 (m, 2H), 6.80 (d, J=8.1 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H), 6.42 (s, 2H), 4.79 (s, 1H), 4.66 (s, 2H), 3.81-3.78 (m, 12H).

Workup

  1. customprecipitates
  2. filtrationThe precipitates were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-bc99fed4f3644e39a4b30b83b4855158
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

Loading…