O-Phenylenediamine → HCID 67153843, compound

HRID 714311Notes

Reaction equation

HRID 714311 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=1)[C:13]([OH:15])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.O[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=N1.Cl.C(N=C=NCCCN(C)C)C.C1(N)C=CC=CC=1N>CN(C)C=O.C(OCC)(=O)C>[NH2:29][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH:31][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][N:18]=[C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:11]=1

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 67153843HCID 67153843, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-benzamidoisonicotinic acid (0.50 g, 2.06 mmol), N,N-diisopropylethylamine (1.10 mL, 6.32 mmol), 1-hydroxybenzotriazole (0.418 g, 3.09 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.59 g, 3.09 mmol) in N,N-dimethylformamide (25 mL) was stirred for 15 minutes at ambient temperature and 1,2-phenylenediamine (0.22 g, 2.06 mmol) was added. The resulting solution was stirred for 20 hours at ambient temperature, diluted with ethyl acetate (75 mL), washed with saturated aqueous sodium bicarbonate solution (50 mL) and water (50 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was triturated with diethyl ether to give N-(2-aminophenyl)-2-benzamidoisonicotinamide as an off-white solid (0.37 g, 53%): MS (ES+) m/z 333.5 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (50 mL) and water (50 mL)
  2. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8e645638542543678603904255692440
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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