4-Pyridinecarboxaldehyde → HCID 58989996, compound

HRID 1663059Notes

Reaction equation

HRID 1663059 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:12]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][CH2:18][C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 27249674-Fluoroanthranilic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58989996HCID 58989996, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred mixture of 2-amino-4-fluorobenzoic acid (Aldrich, 2.0 g) and pyridine-4-carbaldehyde (1.21 ml) in 1,2-dichloroethane (20 ml) was added sodium triacetoxy-borohydride (4.1 g). The reaction mixture was stirred at room temperature for 18 hours. Silica gel was added and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (elution with EtOAc/methanol 19/1, v/v) and gave the title compound (1.04 g). 13C-NMR (DMSO-d6) δ 169.1, 166.2, 152.5, 149.6, 148.2, 134.6, 121.9, 107.6, 102.1, 97.7, 44.6.

Workup

  1. additionSilica gel was added
  2. customthe solvent was evaporated under reduced pressure
  3. washelution with EtOAc/methanol 19/1

Sources & evidence

ORD record
ord-c924ed1e9406424892c86e6afb35a820
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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