O-Phenylenediamine → HCID 86600975, compound

HRID 1908987Notes

Reaction equation

HRID 1908987 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](O)=O)[CH:5]=[CH:4][CH:3]=1.[C:11]1([NH2:18])[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=1>>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[NH:18][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7243O-PhenylenediamineHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 86600975HCID 86600975, compoundYield 65%

Conditions

Temperature
220 °C

Procedure

The mixture of 6-Bromopyridine-2-carboxylic acid (2.01 g, 10 mmol) and benzene-1,2-diamine (1.08, 10 mmol) in polyphosphoric acid was heated at 220° C. for 4 h. The solution was poured into ice-water, and the formed precipitate was collected by filtration and further washed with NaHCO3 and water. After recrystallization in ethanol, the desired product was obtained in yield of 65% (1.76 g). 1H NMR (400 MHz, CDCl3, ppm): 8.31 (d, 2H, J=7.2 Hz), 8.03 (t, 1H, J=7.6 Hz), 7.63 (m, 2H), 7.24 (s, 2H). 13C NMR (100 MHz, CDCl3): 150.20, 148.63, 142.46, 139.46, 135.32, 129.87, 128.04, 124.30, 123.29, 122.92, 120.21, 110.09.

Workup

  1. filtrationthe formed precipitate was collected by filtration
  2. washfurther washed with NaHCO3 and water
  3. customAfter recrystallization in ethanol

Sources & evidence

ORD record
ord-e37533ae6a164ab680da41125a308482
Source dataset
uspto-grants-2013_12
Patent number
US08598351B2

Reaction notes

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