O-Phenylenediamine → o-Aminoacetanilide

HRID 1487235Notes

Reaction equation

HRID 1487235 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>ClCCl>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 7918Acetic Anhydride

Product 1

HCID 11149o-AminoacetanilideYield 18.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzene-1,2-diamine (100 g, 0.93 mol) in dichloromethane (1 L) at 0° C. was added acetic anhydride (87 mL, 0.92 mol). After stirring at 0° C. for 2 hours, the mixture was stand at 0° C. for 12 hours and the precipitate was collected by filtration, washed by dichloromethane and ether, dried in air to afford the product N-(2-aminophenyl)acetamide (25 g, yield 18%). 1H NMR (400 MHz, CDCl3) δ ppm 7.14-7.26 (m, 2H), 7.04-7.08 (m, 1H), 6.78-6.81 (m, 2H), 3.86 (br s, 2H), 2.20 (s, 3H).

Workup

  1. customat 0° C.
  2. customfor 12 hours
  3. filtrationthe precipitate was collected by filtration
  4. washwashed by dichloromethane and ether
  5. customdried in air

Sources & evidence

ORD record
ord-2c796601d27844e780caace5863f4817
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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