4-Aminobenzoic Acid → HCID 178419751, compound

HRID 1404846Notes

Reaction equation

HRID 1404846 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:2]=1.N[C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.[N:22]#[C:23][Br:24]>CO>[BrH:24].[C:9]([CH2:8][CH2:7]/[C:3](/[CH:2]=[N:22]/[C:23]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)=[CH:4]\[CH:5]=[CH:6]\[NH:1][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 10476Cyanogen BromideHCID 2596243-(Pyridin-3-yl)propanoic acid

Product 1

HCID 178419751HCID 178419751, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-Pyridinepropionic acid (10 mmol, 1.52 g) and 4-aminobenzoic acid (20 mmol, 2.74 g) were dissolved in 75 mL methanol on an ice water bath. Cyanogen bromide (10 mmol, 1.07 g) in 5 mL methanol was then added to the reaction solution over 5 min. The product, (1.02 g, 21%), was collected by filtration after stirring for 2 hours and was washed with dichloromethane. 1H NMR (500 MHz, DMSO-d6): δ 12.40 (s, 3H), 7.95-7.83 (m, 5H), 7.67-7.65 (m, 1H), 7.17 (d, 2H, J=8.0 Hz), 7.09 (d, 2H, J=8.5 Hz), 6.95 (d, 1H, J=10.5 Hz), 6.17 (t, 1H, J=12.3 Hz), 2.71 (t, 2H, J=7.5 Hz), 2.40 (t, 2H, J=7.8 Hz). ESI [M+H]+ m/z calcd. for [C22H2iN2O6]+ 409.4, found 409.3.

Workup

  1. filtrationThe product, (1.02 g, 21%), was collected by filtration
  2. washwas washed with dichloromethane

Sources & evidence

ORD record
ord-4c80ddf69ca5493e96e8287c11a2865b
Source dataset
uspto-grants-2014_12
Patent number
US08916137B2

Reaction notes

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