3-Methoxybenzaldehyde → HCID 56620055, compound

HRID 1247935Notes

Reaction equation

HRID 1247935 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].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O.C[O-].[Na+]>CO>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[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

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 10942334Sodium MethoxideHCID 13251342HCID 13251342, compound

Product 1

HCID 56620055HCID 56620055, 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. (3.3 g) was reacted with 3-methoxybenzaldehyde (5.52 g) in methanol (145 g) in the presence of sodium methoxide (2.97 g) under stirring at reflux temperature for 144 hours. After cooling the precipitate was filtered and treated with formic acid and then with water: the crude compound was recovered by filtration, washed with water until neutral and crystallized from CH2Cl2 /methanol to give 2.73 g of 3-(3-methoxy-benzylidene)-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid, m.p. 310°-312° C., NMR (CF3COOD) δ ppm: 3.42 (br) (4H, cyclopentane protons), 4.11 (s) (3H, OCH3), 7.2-7.6 (m) (4H, phenyl protons), 7.61 (br) (1H, =CH--), 8.41 (d) (1H, C-5 proton), 9.11 (d.d) (1H, C-6 proton), 10.20 (d) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 144 hours
  2. temperatureAfter cooling the precipitate
  3. filtrationwas filtered
  4. additiontreated with formic acid
  5. filtrationwith water: the crude compound was recovered by filtration
  6. washwashed with water until neutral and
  7. customcrystallized from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-ac6fb75cd39b4bf5bc23fb98b00d57a2
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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