Hydrochloric Acid → 3-Methyl-4-nitrobenzonitrile

HRID 1087123Notes

Reaction equation

HRID 1087123 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH2:7])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]#[N:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 5959003-Methyl-4-nitrobenzamide

Product 1

HCID 28014343-Methyl-4-nitrobenzonitrileYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred, 0° C. solution of 3-methyl-4-nitrobenzamide (30 g, 0.169 mol) in dichloromethane (900 mL) under nitrogen was added pyridine (29.5 g, 0.373 mol), then dropwise trifluoroacetic anhydride (42.7 g, 0.203 mol) in dichloromethane (90 mL). The reaction mixture was stirred at 0° C. for one hour and then 1N HCl was added. The organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure to afford 25.5 g (93%) of the 3-methyl-4-nitrobenzonitrile as a light yellow solid; m.p. 69°-71° C.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b830a3aaa8c5415f9c4da848718c690f
Source dataset
uspto-grants-1991_07
Patent number
US05034410

Reaction notes

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