Ethyl cyanoacetate → 1-methyl-3-oxo-3H-benzo[f]chromene-2-carbonitrile

HRID 564749Notes

Reaction equation

HRID 564749 reaction equation
[CH3:1][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:14])=O.[C:15]([CH2:17][C:18](OCC)=[O:19])#[N:16]>[O-]CC.[Na+]>[CH3:1][C:2]1[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:7]=[CH:6][C:5]=2[O:14][C:18](=[O:19])[C:17]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 684551-(2-Hydroxy-1-naphthyl)ethan-1-one

Product 1

HCID 9009071-methyl-3-oxo-3H-benzo[f]chromene-2-carbonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a mixture of sodium ethoxide (100 ml; prepared from 1.38 g sodium and 100 ml ethanol) and 2-hydroxy-1-acetonaphthone (11.29 g, 0.06 mol) was added ethyl cyanoacetate (11.1 ml, 0.1 mol). The resulting mixture was stirred at reflux temperature for 2 h. The reaction mixture was cooled in a ice bath and the precipitate was filtered off and washed with water (20 ml) and cold ethanol (3×20 ml), dried in vacuo at 50° C. for 18 h which afforded (9 g) of crude product. The crude product (9 g) was recrystallised from a mixture of acetone (1 l) and water (25 ml) affording 5.33 g (38%) of 1-methyl-3-oxo-3H-benzo[f]chromene-2-carbonitrile as a solid.

Workup

  1. temperatureat reflux temperature for 2 h
  2. temperatureThe reaction mixture was cooled in a ice bath
  3. filtrationthe precipitate was filtered off
  4. washwashed with water (20 ml) and cold ethanol (3×20 ml)
  5. customdried in vacuo at 50° C. for 18 h which
  6. customafforded (9 g) of crude product
  7. customThe crude product (9 g) was recrystallised from a mixture of acetone (1 l) and water (25 ml)

Sources & evidence

ORD record
ord-49b00149dc664e07b2a4675b5e691bb0
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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