Nitric Acid → 6-Acetamido-3-butyl-5-nitro-phthalide

HRID 2120189Notes

Reaction equation

HRID 2120189 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]([CH2:19][CH2:20][CH2:21][CH3:22])[O:14][C:15]2=[O:16])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]>>[C:5]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]([CH2:19][CH2:20][CH2:21][CH3:22])[O:14][C:15]2=[O:16])=[CH:11][C:10]=1[N+:1]([O-:4])=[O:2])(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 232747896-Acetamido-3-butyl-phthalide

Product 1

HCID 234391106-Acetamido-3-butyl-5-nitro-phthalide

Procedure

To 100 ml of stirred and ice-cold turning nitric acid (sp. gr. 1.50) there are added, in portions, 59 g (0.288 mol) of compound obtained in Example 7 with the temperature below 10° C. The resulting clear solution is put aside at room temperature overnight. The reaction material is poured into crushed ice, and the solid is filtered, washed with water, dried and crystallised from ethanol, giving the title compound.

Workup

  1. additionThe reaction material is poured
  2. custominto crushed ice
  3. filtrationthe solid is filtered
  4. washwashed with water
  5. customdried
  6. customcrystallised from ethanol

Sources & evidence

ORD record
ord-aae83b5e83bf44a2b51f533fcb26b36a
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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