4-Chloroaniline → HCID 3097922, compound

HRID 2272699Notes

Reaction equation

HRID 2272699 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 3097922HCID 3097922, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-chloro-3-nitropyridine (15.4 g, 97.1 mmol) in N,N-dimethylformamide (100 mL) were added 4-chloroaniline (12.4 g, 97.2 mmol) and potassium carbonate (20 g, 140 mmol). The reaction mixture was stirred at 100° C. for 18 hours, and then poured into ice-water (200 mL). The precipitate was collected via filtration and washed with water (3×30 mL) to provide the product as a black solid. Yield: 15 g, 60 mmol, 62%. 1H NMR (400 MHz, DMSO-d6) δ 9.97 (br s, 1H), 8.47-8.57 (m, 2H), 7.69 (d, J=8.8 Hz, 2H), 7.41 (d, J=8.8 Hz, 2H), 7.01 (dd, J=8.2, 4.6 Hz, 1H).

Workup

  1. filtrationThe precipitate was collected via filtration
  2. washwashed with water (3×30 mL)

Sources & evidence

ORD record
ord-15766e19115b4c2482bfca82a3c7b4b3
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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