Nitric Acid → Methyl 5-cyano-2-hydroxy-3-nitrobenzoate

HRID 2093633Notes

Reaction equation

HRID 2093633 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])#[N:6]>C(OCC)(=O)C>[C:5]([C:7]1[CH:8]=[C:9]([N+:1]([O-:4])=[O:2])[C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])#[N:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 68725798Methyl 5-cyano-2-hydroxy-3-nitrobenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 25 ml of fuming nitric acid was added 2.50 g of methyl 5-cyano-2-hydroxybenzoate. This solution quickly turned dark orange, and the reaction was complete after stirring for 1 h. The solution was slowly transferred to 100 ml of ice-cold water. To the resultant suspension was added 100 ml of ethyl acetate and the biphasic mixture was shaken and separated. The aqueous layer was extracted with ethyl acetate (2×60 ml), and the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in ethyl acetate (100 ml) and filtered through a small plug of silica gel, eluting with more ethyl acetate (50 ml). The eluent was concentrated in vacuo to provide the title compound (2.71 g, 87%). Mass spectrum (ESI) 221.2 (M−1).

Workup

  1. stirringthe biphasic mixture was shaken
  2. customseparated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×60 ml)
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered through a small plug of silica gel
  8. washeluting with more ethyl acetate (50 ml)
  9. concentrationThe eluent was concentrated in vacuo

Sources & evidence

ORD record
ord-346694752e6b40a88d081ee526ef569c
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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