Nitric Acid → HCID 21468827, compound

HRID 743863Notes

Reaction equation

HRID 743863 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]#[N:18])=[CH:7][CH:6]=1)C(C)=O.[N+:19]([O-])([OH:21])=[O:20]>S(=O)(=O)(O)O>[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([NH2:1])=[CH:6][C:7]=1[N+:19]([O-:21])=[O:20])#[N:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23005118HCID 23005118, compound

Product 1

HCID 21468827HCID 21468827, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

4'-Acetamino-2-cyanobiphenyl (0.265 moles, 62.47 g.) was added at -15° to -20° C. to 600 ml of concentrated sulfuric acid. While maintaining the temperature below -15° C., nitric acid (0.278 moles, 17.5 g of 90%) in 200 ml of concentrated sulfuric acid was added dropwise. The reaction was stirred for 30 minutes following the addition and then for 3 hours at room temperature. The reaction was poured onto ice with vigorous stirring. The precipitate was filtered and dried. The solid was stirred in methanol (6 liters) and 2N sodium hydroxide (11 liters) for 6 hours, filtered and dried. The reaction produced 60 g of 4-(2-Cyanophenyl)-3-nitroaniline. (MS) (MS)

Workup

  1. additionwas added dropwise
  2. additionthe addition
  3. waitfor 3 hours at room temperature
  4. additionThe reaction was poured onto ice with vigorous stirring
  5. filtrationThe precipitate was filtered
  6. customdried
  7. stirringThe solid was stirred in methanol (6 liters)
  8. wait2N sodium hydroxide (11 liters) for 6 hours
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-41b09a6ee6494d83aa2206426975e317
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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