Ethanol → HCID 135482279, compound

HRID 232565Notes

Reaction equation

HRID 232565 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]1[NH:14][C:15](=[O:23])[C:16]2[N:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)[CH3:2].C(O)C.[OH-].[Na+].ClCCl>O>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:13]2[NH:14][C:15](=[O:23])[C:16]3[N:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 135515411HCID 135515411, compound

Product 1

HCID 135482279HCID 135482279, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2-(2-ethoxy-5-nitrophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one (Example 19; 1.1 g, 0.00353 mol), stannous chloride dehydrate (4.0 g, 0.0177 mol) and ethanol (15 ml) was heated under reflux for 4 hours. The resulting mixture was allowed to cool, diluted with water (15 ml), adjusted to pH 8 with 2N aqueous sodium hydroxide solution, vigorously shaken with dichloromethane (30 ml), and then this mixture filtered. The aqueous phase was separated and extracted further with dichloromethane (2×30 ml), and the organic extracts were then combined, dried (MgSO4) and evaporated under vacuum. Crystallisation of the product from acetonitrile gave the title compound as a hydrated yellow solid (0.72 g, 72%), m.p. 208°-210° C. Found: C,62.88; H,4.88; N,19.67. C15H14N4O2 ;0.25H2O requires C,62.81; H,5.10; N,19.54%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. filtrationthis mixture filtered
  5. customThe aqueous phase was separated
  6. extractionextracted further with dichloromethane (2×30 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated under vacuum
  9. customCrystallisation of the product from acetonitrile

Sources & evidence

ORD record
ord-e2efc5f3c7fc4e22b2c7d29f9d4c5c5f
Source dataset
uspto-grants-1997_01
Patent number
US05591742

Reaction notes

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