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

HRID 490830Notes

Reaction equation

HRID 490830 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].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25]>>[NH2:26][C:22]1[O:1][C:2]2[C:10]([CH:17]([C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=3)[C:23]=1[C:24]#[N:25])=[CH:9][CH:8]=[C:7]1[N:6]([CH3:11])[CH:5]=[CH:4][C:3]=21

Participants

4

Reactant 3

HCID 8010MalononitrileHCID 115693-MethoxybenzaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 100195952-Amino-3-cyano-4-(3-methoxyphenyl)-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-methoxybenzaldehyde (38 mg, 0.27 mmol) and malononitrile (18 mg, 0.27 mmol) similar to Example 24 to yield 64 mg (69%) of white solids. 1H NMR (CDCl3): 7.23-7.18 (m, 1H), 7.05-7.00 (m, 2H), 6.83-6.74 (m, 4H), 6.56 (d, J=3.0 Hz, 1H), 4.81 (s, 1H), 4.64 (brs, 2H), 3.76 (s, 6H).

Sources & evidence

ORD record
ord-cc17c7385d2d4ca588d043b91c968f53
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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