O-Phenylenediamine → HCID 57721164, compound

HRID 1985997Notes

Reaction equation

HRID 1985997 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5](O)=O.[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].[OH-].[Na+].C(=O)(O)[O-].[Na+]>Cl>[OH:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:19]=2)[CH:8]=[C:9]([OH:11])[CH:10]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 74243,5-Dihydroxybenzoic AcidHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 57721164HCID 57721164, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3,5-Dihydroxybenzoic acid (21.4 g, 0.14 mol) and o-phenylenediamine (10 g, 0.093 mol) were refluxed in 4M hydrochloric acid (200 mL) at 135° C. for 24 hours under nitrogen. The mixture was cooled to room temperature and then neutralized to pH 6 with sodium hydroxide and then to pH 8 with sodium bicarbonate. The precipitated tan-colored product was isolated by filtration and recrystallized from methanol/water (1:4) to yield tan-colored needles (6.2 g). 1H NMR (DMSO-d6):δ 6.36 (1H, t), 7.04 (2H, d), 7.19 (2H, m), 7.47 (1H, d), 7.62 (1H, d), 9.56 (O—H,2H, s), 12.71 (N—H, 1H, s).

Workup

  1. customThe precipitated tan-colored product was isolated by filtration
  2. customrecrystallized from methanol/water (1:4)

Sources & evidence

ORD record
ord-4282391c33744b729804e20f3e75774a
Source dataset
uspto-grants-2009_06
Patent number
US07547756B2

Reaction notes

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