Acetic Acid → HCID 178474467, compound

HRID 1651054Notes

Reaction equation

HRID 1651054 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25]C(=O)C)=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:29])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178474468HCID 178474468, compound

Product 1

HCID 178474467HCID 178474467, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.95 g of 2-acetamido-4- hydroxy-6-[2-(4-acetoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 50 mL of water was added 1N aqueous sodium hydroxide until a homogenous solution was obtained. Acidification with acetic acid resulted in the formation of a yellow precipitate which was collected by filtration. The filter cake was washed sequentially with water, methanol, acetone and ether. The residual solid was recrystallized from DMF to give 0.65 g (77%) of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)-ethenyl]pyrido[2,3-d]pyrimidine, as a microcrystalline yellow solid, mp>300° C.; NMR (TFA-d ) delta 2.5 (s, 3H), 6.85, 7.32 (AB q, 2H, J=12 Hz), 7.45, 8.18 (AB q, 4H, J=9 Hz), 8.65 (s, 1H), 9.02 (s, 1H); IR (Nujol) 3300-2200 (br), 1685, 1655, 1630, 1600, 1565 cm-1. MS: Calc'd. for C 18 H14N4O4 : 350. Found: m/e 350 (base), 308

Workup

  1. customwas obtained
  2. filtrationwas collected by filtration
  3. washThe filter cake was washed sequentially with water, methanol, acetone and ether
  4. customThe residual solid was recrystallized from DMF

Sources & evidence

ORD record
ord-c1f5350ef8f04e10be86cca0e0b0f609
Source dataset
uspto-grants-1990_05
Patent number
US04927828

Reaction notes

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