Benzaldehyde → HCID 56627317, compound

HRID 1247940Notes

Reaction equation

HRID 1247940 reaction equation
[CH3:1][O:2][C:3]1[C:8]2=[N:9][C:10]3[CH2:16][CH2:15][CH2:14][C:11]=3[C:12](=[O:13])[N:7]2[CH:6]=[CH:5][CH:4]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[O-].[Na+]>CO>[CH:17](=[C:16]1[C:10]2[N:9]=[C:8]3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][N:7]3[C:12](=[O:13])[C:11]=2[CH2:14][CH2:15]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10942334Sodium MethoxideHCID 20280242HCID 20280242, compound

Product 1

HCID 56627317HCID 56627317, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-methoxy-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one, m.p. 212°-214° C., (4 g) was reacted with benzaldehyde (8 g) in methanol (150 ml) in the presence of sodium methoxide (4 g) at reflux temperature for 150 hours. After cooling and concentration in vacuo to a small volume the precipitate was filtered and washed with water until neutral: crystallization from dioxane gave 2.5 g of 3-benzylidene-5-methoxy-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one, m.p. 229°-230° C., NMR (DMSO d6) δ ppm: 3.26 (bs) (4H, C-1 and C-2 protons), 4.20 (s) (3H, OCH3), 7.5-7.9 (m) (8H, =CH, C-6 and C-7 and phenyl protons), 8.90 (d.d) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 150 hours
  2. temperatureAfter cooling
  3. concentrationconcentration in vacuo to a small volume the precipitate
  4. filtrationwas filtered
  5. washwashed with water until neutral:
  6. customcrystallization from dioxane

Sources & evidence

ORD record
ord-3d76a4e7b9ea4c07823fbe03ff742f93
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

Loading…