Ammonia → HCID 19990455, compound

HRID 346165Notes

Reaction equation

HRID 346165 reaction equation
[NH3:1].[C:2]([C:5]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10](OC)=[CH:9][C:6]=1[C:7]#[N:8])(=[O:4])[CH3:3]>CS(C)=O>[C:2]([C:5]1[C:6]([C:7]#[N:8])=[CH:9][C:10]([NH2:1])=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19990435HCID 19990435, compound

Product 1

HCID 19990455HCID 19990455, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Ammonia was bubbled through a solution of 2-acetyl-5-methoxy-4-nitrobenzonitrile (0.80 g. 3.6 mmol) in 10 ml of dry dimethylsulfoxide with stirring at 80° C. for 45 min. Then the solution was poured into 100 ml of ice-water The product was isolated by filtration and washed with water to afford 0.71 g (95%) of the title compound. M.p. 255°-260° C.; 1H-NMR (DMSO-d6): 2.57 (s, 3H, COCH3), 7.50 (s, 1H, ArH), 8.20 (broad s, 2H, NH2), 8.65 (s, 1H, ArH).

Workup

  1. customwas isolated by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-358d4cff952645b1b21c748f4f7f4a07
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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