Nitric Acid → 5-Nitro-4-ethylisatin

HRID 22184Notes

Reaction equation

HRID 22184 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:17])[C:10](=[O:16])[NH:11]2)[CH3:6]>>[N+:1]([C:15]1[C:7]([CH2:5][CH3:6])=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:16])[C:9]2=[O:17])([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 138270824-Ethyl-1H-indole-2,3-dione

Product 1

HCID 152831765-Nitro-4-ethylisatinYield 52%

Procedure

A beaker containing 15 mL of 90% fuming nitric acid was cooled in an ice-water bath. 2.1 g (12 mmoles) 4-ethylisatin was added in small portions over a five-minute period. The resultant red-orange solution was stirred while in the ice-water bath for 5 minutes, then warmed to room temperature and stirred for another 10 minutes. A yellow solid precipitated immediately when this solution was poured over crushed ice. 1.4 g (52% yield) 5-nitro-4-ethylisatin was obtained. NMR(CDCl3): 1.29(t,3H, J=7.5 Hz), 3.11(q,2H,J=7.5 Hz), 7.11 (d,1H,J=8.7 Hz), 8.27 (d,1H,J=8.7 Hz), 9.46(bs,1H). MS(m/z): 220(M+).

Workup

  1. temperaturewas cooled in an ice-water bath
  2. customA yellow solid precipitated immediately when this solution
  3. additionwas poured
  4. customover crushed ice

Sources & evidence

ORD record
ord-85f9806f08b2446c91781bba9b3d0d8a
Source dataset
uspto-grants-1995_06
Patent number
US05428021

Reaction notes

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