3-Cyano-7-hydroxy-4-methylcoumarin → HCID 136387768, compound

HRID 579438Notes

Reaction equation

HRID 579438 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])=[C:7]([C:13]#[N:14])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[NH4+]=[S:17]>CN(C)C=O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])=[C:7]([C:13](=[S:17])[NH2:14])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 53931723-Cyano-7-hydroxy-4-methylcoumarin

Product 1

HCID 136387768HCID 136387768, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-Hydroxy-4-methyl-2-oxo-2H-chromene-3-carbonitrile (7.50 g, 37.31 mmol) in N,N-dimethylformamide (150 mL), ammonium sulfide (40-48 wt. % solution in water; 38 mL, 560 mmol) was added, and the resulted mixture was stirred at room temperature for a week. An additional portion of ammonium sulfide (38 mL) was added on every second day. The solution was evaporated and the solid residue was triturated with water, filtered and dried. The obtained crude product was purified by column chromatography (Kieselgel 60), with chloroform-methanol (1:1) as eluent. The title compound (3.20 g, 13.6 mmol, 36%) was isolated as a yellow powder,

Workup

  1. customThe solution was evaporated
  2. customthe solid residue was triturated with water
  3. filtrationfiltered
  4. customdried
  5. customThe obtained crude product
  6. customwas purified by column chromatography (Kieselgel 60), with chloroform-methanol (1:1) as eluent

Sources & evidence

ORD record
ord-30b67dfb2de145eeaae157fb6a32826c
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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