Benzaldehyde → HCID 10364246, compound

HRID 2252089Notes

Reaction equation

HRID 2252089 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH:7]=1.[CH:25]1[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=1.[BH4-].[Na+].[OH-].[Na+]>CCO.[Cl-].[Na+].O>[CH2:31]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH:7]=1)[C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 58958050HCID 58958050, compound

Product 1

HCID 10364246HCID 10364246, compoundYield 456.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-(2-Aminoethyl)-3-(2-methylquinolin-4-ylamino)benzamide (50). A mixture of methyl ester 49 (2.0 g, 6.8 mmol) and ethylenediamine (30 mL) was heated at 110° C. for 2 hours before it was poured into ice water (300 mL). The precipitate was filtered and dried under high vaccum to give 50 (2.0 g, 91%) as an off-white solid, which was used without further purification. Step 2. N-(2-Benzylaminoethyl)-3-(2-methylquinolin-4-ylamino)benzamide. A solution of amine 50 (0.22 g, 0.68 mmol) and benzyaldehyde (0.07 mL, 0.08 mmol) in EtOH (3.0 mL) was heated at reflux overnight before it was allowed to cool to room temperature. Sodium borohydride (0.04 g, 0.80 mmol) was added and the reaction was stirred at room temperature for 1 hour. The mixture was mixed with 2N NaOH (3.0 mL), brine (2.0 mL), and extracted with 7:3 CH2Cl2/MeOH (3×5.0 mL). The combined organic layers were dried (K2CO3) and concentrated under reduced pressure. The residue was purified by flash chromatrography (SiO2, gradient elution, 3:1 hexanes/EtOAc to 7:3 CH2Cl2/MeOH) to yield the desired product (0.15 g, 62%) as a pale yellow solid.

Workup

  1. customwas used without further purification
  2. temperatureat reflux overnight before it
  3. extractionextracted with 7:3 CH2Cl2/MeOH (3×5.0 mL)
  4. dry with materialThe combined organic layers were dried (K2CO3)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatrography (SiO2, gradient elution, 3:1 hexanes/EtOAc to 7:3 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-e61c34aae21d49079f4cc7864ae135e6
Source dataset
uspto-grants-2008_01
Patent number
US07320989B2

Reaction notes

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