Nitric Acid → HCID 19990462, compound

HRID 346135Notes

Reaction equation

HRID 346135 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:16])=[CH:10][C:7]=1[C:8]#[N:9]>>[Cl:5][C:6]1[C:7]([C:8]#[N:9])=[CH:10][C:11]([NH:14][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:16])=[C:12]([N+:1]([O-:4])=[O:2])[CH:13]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 19990461HCID 19990461, compound

Product 1

HCID 19990462HCID 19990462, compoundYield 86%

Procedure

To 75 ml ice-cooled 100% nitric acid was added gradually 8.1 g (32.1 mmol) 2-chloro-5-ethoxalylaminobenzonitrile. Stirring was continued at 0° C. for 1.5 h, and then the reaction mixture was poured into 500 ml ice-water. The precipitated product was filtered off and recrystallized (ethanol-water) to give 8.25 g (86%) of 6-chloro-3-ethoxalylamino-4-nitrobenzonitrile. M.p. 143-45° C. 1H-NMR (CDCl3 -DMSO-d6): 11.3 (1H, broad s), 8.1 (2H, dd, J=10 Hz), 4.3 (2H, q), 1.4 (3H, t). The filtrate was extracted with 150 ml ethylacetate to give 2-chloro-3-ethoxalylamino-4-nitrobenzonitrile as an oil (0.67 g, 7%). 1H-NMR (CDCl3 -DMSO-d6) 11.4 (1H, broad s), 8.57 (1H, s), 8.33 (1H, s), 4.3 (2H, q), 1.4 (3H, t).

Workup

  1. filtrationThe precipitated product was filtered off
  2. customrecrystallized (ethanol-water)

Sources & evidence

ORD record
ord-66f86fde43bb469687445c97368f6cd3
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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