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

HRID 1088667Notes

Reaction equation

HRID 1088667 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 (see part (b)) (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 title compound was obtained as a yellow solid which was filtered off and dried in vacuo, (9.80 g, 70%) m.p. 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

Sources & evidence

ORD record
ord-d16cc7fcadb9407081a3e0c242da770a
Source dataset
uspto-grants-1990_10
Patent number
US04963560

Reaction notes

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