Hydrochloric Acid → HCID 136161598, compound

HRID 232574Notes

Reaction equation

HRID 232574 reaction equation
[OH:1]O.[OH-].[Na+].[C:5]([C:7]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH3:26])[NH:15][C:16](=[O:17])[C:11]=2[N:10]=[CH:9][CH:8]=1)#[N:6].Cl>C(O)C>[C:5]([C:7]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH3:26])[NH:15][C:16](=[O:17])[C:11]=2[N:10]=[CH:9][CH:8]=1)(=[O:1])[NH2:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 135670778HCID 135670778, compound

Product 1

HCID 136161598HCID 136161598, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30% Aqueous hydrogen peroxide solution (0.5 ml) was added to a stirred aqueous sodium hydroxide solution (1M, 40 ml), followed by 8-cyano-2-(2-ethoxyphenyl)pyrido[3,2-d]pyrimidin-4(3H)-one (Preparation 14; 0.2 g, 0.00068 mol) and ethanol (2 ml). The mixture was heated under reflux for 2 hours, allowed to cool, acidified with 1N hydrochloric acid, and then extracted with a mixture of dichloromethane and methanol (10:1, 5×50 ml). The combined organic fractions were evaporated under vacuum and the resulting residue triturated with ethanol to give the title compound as a colourless solid (0.152 g, 72%), m.p. 295°-297° C. Found: C,61.65; H,4.56; N,17.61. C16H14N4O3 requires C,61.93; H,4.55; N,18.06%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. extractionextracted with a mixture of dichloromethane and methanol (10:1, 5×50 ml)
  5. customThe combined organic fractions were evaporated under vacuum
  6. customthe resulting residue triturated with ethanol

Sources & evidence

ORD record
ord-ec031a5ba80b4697a7f1dde92e2e52a5
Source dataset
uspto-grants-1997_01
Patent number
US05591742

Reaction notes

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