Nitric Acid → HCID 57033336, compound

HRID 745586Notes

Reaction equation

HRID 745586 reaction equation
[NH:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]([CH3:17])=[O:16])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)[C:2]([CH3:4])=[O:3].[N+:18]([O-])([OH:20])=[O:19]>C(O)(=O)C>[NH:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]([CH3:17])=[O:16])=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH2:7][CH2:6]1)[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 54454846HCID 54454846, compound

Product 1

HCID 57033336HCID 57033336, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

33 g of 1,5-diacetamino-indoline were dissolved at 70° C. in 120 ml of glacial acetic acid and nitrated dropwise with 15 ml of nitric acid (d=1.4). The reaction became vigorous and methanol/ice cooling was used. The precipitated crystals were removed by filtration under suction, dissolved in methylene chloride and washed neutral. After evaporation and crystallization from isopropanol, there were obtained 25 g (62.8% of theory) of 1,5-diacetamino-6-nitro-indoline of melting point 212°-213° C.

Workup

  1. customThe precipitated crystals were removed by filtration under suction
  2. dissolutiondissolved in methylene chloride
  3. washwashed neutral
  4. customAfter evaporation and crystallization from isopropanol

Sources & evidence

ORD record
ord-ead01e5f7763434e8265d3c20ae8303c
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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