4-Fluorobenzaldehyde → HCID 70590234, compound

HRID 1449017Notes

Reaction equation

HRID 1449017 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(O[C:13](=O)[CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])C.[CH2:27]([O:29][C:30](=[O:35])/[CH:31]=[C:32](\[NH2:34])/[CH3:33])[CH3:28]>C(O)C>[CH2:27]([O:29][C:30]([C:31]1[CH:6]([C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[C:31]([C:30]([O:29][CH2:27][CH3:28])=[O:35])=[C:32]([CH3:33])[NH:34][C:13]=1[CH2:14][N:15]1[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]2[C:19]1=[O:20])=[O:35])[CH3:28]

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 95202Ethyl (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 70590234HCID 70590234, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.4 g of 4-fluorobenzaldehyde, 31 g of phthalimidoacetic acid ethyl ester and 13 g of β-aminocrotonic acid ethyl ester in 100 ccs of ethanol are heated to the boil under reflux for 2×24 hours, the mixture is allowed to cool, whilst stirring, and, after filtering, yellow crystals of melting point 144°-145° C. (ethanol) are obtained, yield: 80%.

Workup

  1. temperatureunder reflux for 2×24 hours
  2. temperatureto cool
  3. filtrationafter filtering
  4. customyellow crystals of melting point 144°-145° C. (ethanol) are obtained

Sources & evidence

ORD record
ord-739991b8495049288236c5dcf09523ef
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

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