2-Methylbenzaldehyde → HCID 56612994, compound
Reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][CH2:16][CH2:17][C:3]1=2.C[O-].[Na+].[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O>CO>[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=[C:15]1[C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][N:7]3[C:2](=[O:1])[C:3]=2[CH2:17][CH2:16]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid (3.12 g) in methanol (145 ml) containing 2.9 g of sodium methoxide was reacted with 4.86 g of 2-methyl-benzaldehyde under stirring at reflux temperature for 144 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 1.9 g of 3-(2-methyl-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid, m.p. 300°-302° C., NMR (CF3COOD) δ ppm: 2.49 (s) (3H, --CH3), 3.36 (s) (4H, cyclopentane protons), 7.42 (m) (3H, phenyl protons), 7.64 (m) (1H, phenyl proton), 7.81 (bs) (1H, =CH--), 8.40 (d) (1H, C-5 proton), 9.11 (d d) (1H, C-6 proton), 10.23 (d) (1H, C-8 proton).
Workup
- temperatureat reflux temperature for 144 hours
- temperatureAfter cooling
- concentrationconcentration in vacuo to a small volume
- filtrationthe precipitate was filtered
- additiontreated with acetic acid
- filtrationwith water: the crude compound was recovered by filtration
- washwashed with water until neutral and
- customcrystallized from CH2Cl2 /methanol
Sources & evidence
- ORD record
- ord-654333190e8141a6b96b758c68c33d5a
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04521419
Reaction notes
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