3-Nitrobenzaldehyde → 2-Amino-3-cyano-4-(3-nitrophenyl)-7-methyl-4H-pyrrolo[2,3-h]chromene

HRID 490828Notes

Reaction equation

HRID 490828 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:11].[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].[C:23](#[N:27])[CH2:24][C:25]#[N:26]>>[NH2:27][C:23]1[O:1][C:2]2[C:10]([CH:18]([C:17]3[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=3)[C:24]=1[C:25]#[N:26])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH:5]=[CH:4][C:3]=21

Participants

4

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 8010MalononitrileHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 104503062-Amino-3-cyano-4-(3-nitrophenyl)-7-methyl-4H-pyrrolo[2,3-h]chromene

Procedure

The title compound was prepared from 4-hydroxy-1-methylindole (40 mg, 0.27 mmol), 3-nitrobenzaldehyde (41 mg, 0.27 mmol) and malononitrile (18 mg, 0.27 mmol) similar to Example 24 to yield 61 mg (65%) of white solids. 1H NMR (CDCl3): 8.10 (d, J=7.8 Hz, 1H), 8.05-8.04 (m, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.49 (t, J=7.8 Hz, 1H), 7.08-7.02 (m, 2H), 6.69 (d, J=8.7 Hz, 1H), 6.59 (d, J=3.0 Hz, 1H), 5.00 (s, 1H), 4.76 (s, 2H), 3.78 (s, 3H).

Sources & evidence

ORD record
ord-58308209b05f49c0b434195155dae1e5
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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