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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 490824Generated: October 30, 2026

Malononitrile → 2-Amino-3-cyano-4-(5-methyl-pyridin-3-yl)-7-hydroxymethyl-4H-pyrrolo[2,3-h]chromene

https://huagongshe.com/reaction/490824

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMalononitrileHCID 8010—
ReactantPiperidineHCID 8082—
Reactant5-Methylpyridine-3-carbaldehydeHCID 14141158—
Reactant1-(Hydroxymethyl)-1H-indol-4-olHCID 24776903—
Product2-Amino-3-cyano-4-(5-methyl-pyridin-3-yl)-7-hydroxymethyl-4H-pyrrolo[2,3-h]chromeneHCID 10382083—

Reaction Steps

The title compound was prepared from 1-hydroxymethyl-4-hydroxy-indole (163 mg, 1.0 mmol), 5-methyl-pyridine-3-carbaldehyde (121 mg, 1.0 mmol), malononitrile (66 mg, 1.0 mmol) and piperidine (0.05 mL, 0.5 mmol), similar to Example 16, to yield 230 mg (69%) of a white solid. 1H NMR (DMSO-d6): 8.31 (d, J=2.4 Hz, 1H), 8.27 (d, J=1.8 Hz, 1H), 7.44 (d, J=3.0 Hz, 1H), 7.31-7.26 (m, 2H), 7.01 (brs, 2H), 6.73 (d, J=8.4 Hz, 1H), 6.48-6.47 (m, 2H), 5.47 (d, J=6.0 Hz, 2H), 4.86 (s, 1H), 2.23 (s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07528164B2
Source datasetuspto-grants-2009_05
ORD IDord-a4e300532cc642d0937d8c22361a1c99
Source noteuspto-grants-2009_05