Benzaldehyde → HCID 178468755, compound

HRID 1935718Notes

Reaction equation

HRID 1935718 reaction equation
[NH2:1][C:2]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:16]1([C:15]2[NH:1][C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][C:12]=3[N:13]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 11171330Ethyl 2,3-diaminobenzoate

Product 1

HCID 178468755HCID 178468755, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2,3-diaminobenzoate (3.0 g) in methanol (60 mL) was added 1 N hydrochloric acid (0.6 mL) and benzaldehyde (1.7 mL), and the mixture was stirred at room temperature for 1 hour. After evaporation of the solvent under a reduced pressure, to the solution of the obtained residue in dichloromethane was added silica gel. The solvent was evaporated under a reduced pressure, and the resulting residue was heated at 100° C. for 1 hour. By purifying the reaction mixture by a silica gel column chromatography (eluent:hexane/ethyl acetate), the title compound was obtained as crystal (1.8 g).

Workup

  1. customAfter evaporation of the solvent under a reduced pressure
  2. additionto the solution of the obtained residue in dichloromethane was added silica gel
  3. customThe solvent was evaporated under a reduced pressure
  4. temperaturethe resulting residue was heated at 100° C. for 1 hour
  5. customBy purifying the reaction mixture by a silica gel column chromatography (eluent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-33732d6d20814c18a1bec0794531fe8b
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

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