4-Nitrobenzaldehyde → HCID 4718994, compound

HRID 515793Notes

Reaction equation

HRID 515793 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=1.[BH3-]C#N.[Na+]>ClCCCl>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:19][CH2:18][C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 773174-PyridinemethanamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 4718994HCID 4718994, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-nitrobenzaldehyde (3.0 g, 19.8 mmol), 4-pyridylmethylamine (2.36 g, 21.8 mmol), and NaBH3CN (1.75 g, 27.7 mmol) in 1,2-dichloroethane (40.0 mL) was stirred at room temperature for 36 h and then concentrated to dryness. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (3×). The combined organics were washed with brine (2×), dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (MeOH/DCM=1/400) to afford 1.3 g of N-(4-nitrobenzyl)-1-(pyridin-4-yl)methanamine as brown oil.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organics were washed with brine (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (MeOH/DCM=1/400)

Sources & evidence

ORD record
ord-af8482288c0d45d6840f22e473b9faaf
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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