Sodium Hydroxide → HCID 136186376, compound

HRID 374773Notes

Reaction equation

HRID 374773 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][CH3:32])[CH:17]=[CH:18][C:19]([O:21]C(C)(C)C)=[O:20])[NH:10][C:9]2=[O:33]>CO>[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][CH3:32])[CH:17]=[CH:18][C:19]([OH:21])=[O:20])[NH:10][C:9]2=[O:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136203549HCID 136203549, compound

Product 1

HCID 136186376HCID 136186376, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Aqueous sodium hydroxide solution (2.8 ml) was added to a stirred solution of t-butyl 3-(8-methylquinazolin-4(3H)-on-2-yl)-4n-propoxycinnamate (Example 10; 0.79 g, 0.0018 mol) in methanol (2.8 ml) and the resulting solution heated under reflux for 4 hours. The solvent was removed by evaporation under vacuum, the residue-dissolved in water (25 ml) and this solution washed with ethyl acetate (4×30 ml). The aqueous solution was acidified with 2N hydrochloric acid and then extracted with ethyl acetate (3×30 ml). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum to give the title compound, which crystallized from ethyl acetate to give a white solid (0.41 g, 60%), m.p. 256°-257° C. Found: C,69.46; H,5.57; N,7.75. C21H20N4O4 requires C,69.22; H,5.53; N,7.69%.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureunder reflux for 4 hours
  3. customThe solvent was removed by evaporation under vacuum
  4. dissolutionthe residue-dissolved in water (25 ml)
  5. washthis solution washed with ethyl acetate (4×30 ml)
  6. extractionextracted with ethyl acetate (3×30 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-601797a7954c46d483d7c4ab68024ae8
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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