Nitric Acid → SINITRODIL,6-NITRO

HRID 374438Notes

Reaction equation

HRID 374438 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[O:9][CH2:8]1)([O-:3])=[O:2].[N+:18]([O-])([OH:20])=[O:19]>>[N+:1]([O:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:10]=2[O:9][CH2:8]1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 121985Sinitrodil

Product 1

HCID 10379071SINITRODIL,6-NITRO

Procedure

50 ml of 100% fuming nitric acid were dropped into 50 g (0.21 mole) of 2,3-dihydro-3-(2'-nitrooxyethyl)-4H-1,3-benzoxazin-4-one, at a temperature of -10° C. At the end of the addition, the reaction mixture was stirred for minutes, then poured in ice and sequentially extracted with chloroform. The organic layer was washed with water, sodium hydroxide 0.1N and again with water, then dried over sodium sulphate and concentrated to dryness. The resulting oil was taken up with warm ethyl ether yielding 42.5 g of the title compound as white solid. m.p. 97°-99° C. (ethyl ether).

Workup

  1. additionAt the end of the addition
  2. additionpoured in ice
  3. extractionsequentially extracted with chloroform
  4. washThe organic layer was washed with water, sodium hydroxide 0.1N and again with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-21fc5dc7adf44ae68a09b74858cf4182
Source dataset
uspto-grants-1996_01
Patent number
US05480882

Reaction notes

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