Benzaldehyde → HCID 54009854, compound

HRID 1247936Notes

Reaction equation

HRID 1247936 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:18]=1)[C:10](=[O:17])[C:11]1[CH2:16][CH2:15][CH2:14][C:12]=1[N:13]=2)=[O:4].C[O-].[Na+].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH:22](=[C:14]1[C:12]2[N:13]=[C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:18][N:9]3[C:10](=[O:17])[C:11]=2[CH2:16][CH2:15]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10942334Sodium MethoxideHCID 13251342HCID 13251342, compound

Product 1

HCID 54009854HCID 54009854, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid methyl ester, m.p. 153°-154° C. (5 g) in methanol (300 ml) containing 6.45 g of sodium methoxide was reacted with 10.9 g of benzaldehyde under stirring at reflux temperature for 96 hours. After cooling and concentration in vacuo to a small volume the precipitate was filtered and treated with acetic acid and then with water; the crude compound was recovered by filtration, washed with water until neutral and crystallized from CH2Cl2 /methanol and then from dioxane to give 3.25 g of 3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid, m.p. 309°-310° C., NMR (CF3COOD) δ ppm: 3.44 (m) (4H, cyclopentane protons), 7.68 (m) (6H, =CH-- and phenyl protons), 8.44 (d) (1H, C-5 proton), 9.15 (d.d) (1H, C-6 proton), 10.23 (d) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 96 hours
  2. temperatureAfter cooling
  3. concentrationconcentration in vacuo to a small volume the precipitate
  4. filtrationwas filtered
  5. additiontreated with acetic acid
  6. filtrationthe crude compound was recovered by filtration
  7. washwashed with water until neutral and
  8. customcrystallized from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-a1fa4299846b42129444e882e0f996e9
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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