Nitric Acid → HCID 14722490, compound

HRID 1655454Notes

Reaction equation

HRID 1655454 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.[C:17]([NH:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)(=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]>>[N+:1]([C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][C:24]=1[NH:23][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])[C:28]([O:30][CH3:31])=[O:29])([O-:4])=[O:2]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 1722038HCID 1722038, compound

Product 1

HCID 14722490HCID 14722490, compoundYield 76%

Procedure

Fuming nitric acid (1.4 ml) was added dropwise to acetic anhydride (12 ml) under ice-cooling and then was added conc. sulfuric acid (0.1 ml). To the stirred mixture was added methyl 4-valerylaminobenzoate (2.3 g) under ice-cooling, followed by stirring for one hour. To the resultant mixture was added ice water, and the crystals separated out were recrystallized from ethyl acetate-hexane to give yellow prisms (2.14 g, 76%), m.p. 106-107° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe crystals separated out
  4. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9b397df367fa47a6b08a38558ed484d2
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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