Benzaldehyde → HCID 54009083, compound

HRID 1380086Notes

Reaction equation

HRID 1380086 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[CH:9][C:8]([NH:12][C:13](=[O:19])[C:14]([O:16]CC)=[O:15])=[CH:7][C:6]=2[N:5]=[C:4]2[CH2:20][CH2:21][CH2:22][N:3]12.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C[O-].[Na+]>CO>[CH:23](=[C:20]1[C:4]2=[N:5][C:6]3[CH:7]=[C:8]([NH:12][C:13](=[O:19])[C:14]([OH:16])=[O:15])[CH:9]=[CH:10][C:11]=3[C:2](=[O:1])[N:3]2[CH2:22][CH2:21]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10942334Sodium MethoxideHCID 86740708HCID 86740708, compound

Product 1

HCID 54009083HCID 54009083, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

N-(9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-amino-oxoacetic acid, ethyl ester, m.p. 198°-200° C. (1.2 g) was reacted with benzaldehyde (0.84 g) in methanol (20 ml), in the presence of sodium methoxide (0.86 g) under stirring at 60° C. for 6 hours. After cooling the reaction mixture was concentrated in vacuo and diluted with ethyl ether: the precipitate was filtered, washed with ether and dissolved in water. Acidification with acetic acid gave a precipitate which was filtered and washed with water: crystallization from formic acid gave 0.4 g of N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-amino-oxoacetic acid, m.p. 220°-225° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with ethyl ether
  4. filtrationthe precipitate was filtered
  5. washwashed with ether
  6. dissolutiondissolved in water
  7. customAcidification with acetic acid gave a precipitate which
  8. filtrationwas filtered
  9. washwashed with water
  10. customcrystallization from formic acid

Sources & evidence

ORD record
ord-f990d858761748f5838bc1d4e5f21454
Source dataset
uspto-grants-1986_04
Patent number
US04579847

Reaction notes

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