O-Phenylenediamine → N-(2-Aminophenyl)-4-cyanobenzamide

HRID 1509990Notes

Reaction equation

HRID 1509990 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].O[C:13]1[C:21]2[N:20]=N[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[NH2:18][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:21]=1[NH:20][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 16790771N-(2-Aminophenyl)-4-cyanobenzamideYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Cyanobenzoic acid (294 mg, 2 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (768 mg, 4 mmol), hydroxybenzotriazole (324 mg, 2.4 mmol), triethylamine (808 mg, 8 mmol) and o-phenylenediamine (432 mg, 4 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give N-(2-aminophenyl)-4-cyanobenzamide (364 mg, 77%) as a grey solid. LC-MS (m/z) 238 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e9647fa11b044b49a37f6f27c4957273
Source dataset
uspto-grants-2012_07
Patent number
US08211901B2

Reaction notes

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