Ethanol → HCID 86646891, compound

HRID 1097231Notes

Reaction equation

HRID 1097231 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[Se:4][C:3]=1[C:11]#[N:12].C([OH:15])C>[OH-].[Na+]>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[Se:4][C:3]=1[C:11]([NH2:12])=[O:15]

Participants

4

Reactant 2

HCID 702EthanolHCID 86646892HCID 86646892, compound

Product 1

HCID 86646891HCID 86646891, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
7.5 °C

Procedure

To a suspension of 3-aminoselenopheno[2,3-b]pyridine-2-carbonitrile (1.0 g) in aqueous sodium hydroxide solution (20 mL, 10%) was added ethanol (20 mL) and the mixture refluxed for 45 min. Ethanol was distilled off under vacuum (appr. 25 mL) and the mixture was allowed to cool to 5-10° C. The separated crystals and the solution was poured into ice cooled water and stirred for 15 min. The solid was filtered off, washed with cold water and dried to give the product as a pale yellow color solid (0.53 g, 50%), mp 256-260° C. 1H NMR (400 MHz, DMSO-d6): δ 8.60 (1H, d, J=3.6 Hz, H-6), 8.37 (1H, d, J=7.6 Hz, H-4), 7.47 (1H, dd, J=8.0, 4.8 Hz, H-5), 7.32 (2H, s, —CONH2), 7.09 (2H, s, —NH2); LC-MS (negative ion mode): m/z 238, 241 (M−H)−.

Workup

  1. temperaturethe mixture refluxed for 45 min
  2. distillationEthanol was distilled off under vacuum (appr. 25 mL)
  3. additionThe separated crystals and the solution was poured into ice
  4. temperaturecooled water
  5. filtrationThe solid was filtered off
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-110f991f7d72418094e544c60c7ac99e
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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