Nitric Acid → HCID 14391496, compound

HRID 346138Notes

Reaction equation

HRID 346138 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:12][C:13]1[CH:14]=[C:15]([C:21]#[N:22])[C:16](=[CH:19][CH:20]=1)[C:17]#[N:18])([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:6].C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:5]([NH:12][C:13]1[CH:14]=[C:15]([C:21]#[N:22])[C:16](=[CH:19][C:20]=1[N+:1]([O-:4])=[O:2])[C:17]#[N:18])([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1140TolueneHCID 14391495Ethyl 2-[(3,4-dicyanophenyl)amino]-2-oxoacetate

Product 1

HCID 14391496HCID 14391496, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 50 ml ice-cooled 100% nitric acid was added gradually 2.0 g (8.2 mmol) 4-ethoxalylaminophthalonitrile. Stirring was continued at 25° C. for 48 h. The reaction mixture was poured into 300 ml ice-water to give 1.6 g crude product. Column chromatography (200 g kiselgel; eluents: toluene containing ethyl acetate) gave 0.7 g (30%) 4-ethoxalylamino-5-nitrophthalonitrile. M.p. 140°-141° C. 1H-NMR (DMSO-d6): 11.7 (1H, s), 8.97 (1H, s), 8.70 (1H, s), 4.4 (2H, q), 1.4 (3H, t), and 0.75 g (32%) 4-ethoxalylamino-3-nitrophthalonitrile. M.p. 140-141° C. 1H-NMR (DMSO-d6) 11.7 (1H, s), 8.4 (2H, dd, J=9Hz), 4,4 (2H, q), 1.4 (3H, t).

Workup

  1. customto give 1.6 g crude product

Sources & evidence

ORD record
ord-b4435749c64c4cf5910d91c45cc32784
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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