4-(Aminomethyl)Benzoic Acid → HCID 53982668, compound

HRID 476608Notes

Reaction equation

HRID 476608 reaction equation
O[CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1)([OH:22])=[O:21]>C(O)C>[C:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][CH:2]=[C:3]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[O:5][CH:4]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:25][CH:24]=1)([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 655264-(Aminomethyl)Benzoic AcidHCID 70350763HCID 70350763, compound

Product 1

HCID 53982668HCID 53982668, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g 3-hydroxymethylidene-flavanone and 9 g 4-carboxybenzylamine in 50 ml dry ethanol is stirred under nitrogen and reflux for 30 minutes. After filtration and washing of the solid with warm ethanol, the filtrate is cooled with an ice bath. A yellow precipitate forms which is filtered, dried and recrystallized in toluene. Pure yellow crystalline 3-[N-(4-carboxybenzyl)amino]methylidene-flavanone is obtained; m.p. 195°-200° C.

Workup

  1. temperaturereflux for 30 minutes
  2. filtrationAfter filtration
  3. washwashing of the solid with warm ethanol
  4. temperaturethe filtrate is cooled with an ice bath
  5. filtrationA yellow precipitate forms which is filtered
  6. customdried
  7. customrecrystallized in toluene

Sources & evidence

ORD record
ord-3f8be571ab7e4211b5422daf0e6be50a
Source dataset
uspto-grants-1989_12
Patent number
US04885298

Reaction notes

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