Sodium Cyanide → 6-Methoxy-9-oxo-9H-xanthene-3-carbonitrile

HRID 425292Notes

Reaction equation

HRID 425292 reaction equation
[C-:1]#[N:2].[Na+].F[C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:21])[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[CH:14][C:13]([O:19][CH3:20])=[CH:12][CH:11]=3>CN(C)C=O>[CH3:20][O:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:21])[C:8]1[CH:7]=[CH:6][C:5]([C:1]#[N:2])=[CH:18][C:17]=1[O:16]2

Participants

4

Reactant 2

HCID 8929Sodium Cyanide2×HCID 578391983-Fluoro-6-methoxy-9H-xanthen-9-one

Product 1

HCID 578392066-Methoxy-9-oxo-9H-xanthene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of finely ground sodium cyanide (1.3 g, 26.5 mmol) and 3-fluoro-6-methoxy-xanthen-9-one (2.3 g, 9.42 mmol) in N,N-dimethylformamide (30 mL) was heated at 100° C. for 4 hours. Sodium cyanide (0.7 g, 14.3 mmol) was added and heating continued an additional hour. The mixture was allowed to cool to room temperature, then poured into ice water (˜150 mL). The product was collected by filtration, washed with water and air dried to give Compound 5i, 1.42 g (60%). MS: m/z 251.9 (MH+). 1H NMR (CDCl3): δ 3.96 (s, 3H), 6.91 (d, 1H, J=2.3 Hz), 7.00 (d of d, 1H, J=2.3 & 8.9 Hz), 7.61 (d of d, 1H, J=1 & 8.1 Hz), 7.79 (d, 1H, J=1 Hz), 8.24 (d, 1H, J=8.9 Hz) and 8.42 (d, 1H, J=8.1 Hz).

Workup

  1. temperatureheating
  2. waitcontinued an additional hour
  3. temperatureto cool to room temperature
  4. filtrationThe product was collected by filtration
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-c429ea13e4d14a8d9f98fff6b87e124f
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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