4-Aminobenzonitrile → 4-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine

HRID 973480Notes

Reaction equation

HRID 973480 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>C(O)C>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([NH:13][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[C:3]=2[N+:10]([O-:12])=[O:11])=[CH:15][CH:16]=1)#[N:19]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 107027254-Chloro-2,6-dimethyl-3-nitropyridine

Product 1

HCID 106119434-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-2,6-dimethyl-3-nitropyridine (9.80 g, 52.5 mmol) and 4-aminobenzonitrile (6.20 g, 52.5 mmol) in ethanol (160 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (200 ml), and washed with saturated aqueous sodium bicarbonate (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give a gum which was crystallised by adding ether (100 ml) and sonicating for 5 minutes. The yellow solid (9.80 g, 70%) was filtered off and dried in vacuo, mp 171°-172° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (200 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (100 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a gum which
  7. customwas crystallised
  8. additionby adding ether (100 ml)
  9. customsonicating for 5 minutes
  10. filtrationThe yellow solid (9.80 g, 70%) was filtered off
  11. customdried in vacuo, mp 171°-172° C.

Sources & evidence

ORD record
ord-06e61569c81549dcb5ccdf58cbbdaa1c
Source dataset
uspto-grants-1991_11
Patent number
US05063237

Reaction notes

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