3,4,5-Trimethoxybenzaldehyde → HCID 56629936, compound

HRID 1247934Notes

Reaction equation

HRID 1247934 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:15]=1)[C:7](=[O:14])[C:8]1[CH2:13][CH2:12][CH2:11][C:9]=1[N:10]=2.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH:21]=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:15]=1)[C:7](=[O:14])[C:8]1[CH2:13][CH2:12][C:11](=[CH:21][C:20]3[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:19]=3)[C:9]=1[N:10]=2

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 10942334Sodium MethoxideHCID 12485586HCID 12485586, compound

Product 1

HCID 56629936HCID 56629936, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-chloro-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one (4 g), prepared according to Example 1, was reacted with 3,4,5-trimethoxy-benzaldehyde (8,87 g) in methanol (160 ml) in the presence of sodium methoxide (1.65 g) at reflux temperature for 140 hours. After cooling the precipitate was filtered, washed with water until neutral and crystallized from CH2Cl2 /methanol to give 4.4 g of 7-chloro-3-(3,4,5-trimethoxy-benzylidene)-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one, m.p. 222°-223° C., NMR (CDCl3) δ ppm: 3.13 (br s) (4H, cyclopentane protons), 3.95 (br s) (9H, --OCH3), 6.82 (s) (2H, phenyl protons), 7.42 (br s) (1H, =CH--), 7.58 (d) (2H, C-5 and C-6 protons), 9.02 (t) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 140 hours
  2. temperatureAfter cooling the precipitate
  3. filtrationwas filtered
  4. washwashed with water until neutral and
  5. customcrystallized from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-c1983604b04f49289f6697984744812b
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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