Nitric Acid → HCID 12066241, compound

HRID 726475Notes

Reaction equation

HRID 726475 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].C(OC(=O)C)(=O)C.[N+:19]([O-])([OH:21])=[O:20].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[N+:19]([C:7]1[NH:6][C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:10])[Cl:11])=[CH:9][CH:8]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic Anhydride2×HCID 3214872-(Trichloroacetyl)pyrroleHCID 516892Sodium Bicarbonate

Product 1

HCID 12066241HCID 12066241, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

21.3 g (0.1 mol) of 2-trichloroacetylpyrrole and 100 ml of acetic anhydride were introduced into a round-bottomed flask. At 0° C., a solution of 4.2 ml of fuming nitric acid, 8 ml of acetic acid and 8 ml of acetic anhydride was added dropwise and the temperature was permitted to increase to room temperature. The reaction medium was poured into ice, the pH adjusted to 8 with sodium bicarbonate, extracted with dichloromethane, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (60-40). There were recovered 5.5 g (21%) of 5-nitro-2-trichloroacetylpyrrole in the form of a dark green oil and 11.2 g of 4-nitro-2-trichloroacetylpyrrole of melting point 160°-163° C.

Workup

  1. additionThe reaction medium was poured into ice
  2. extractionextracted with dichloromethane
  3. customthe organic phase decanted off
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (60-40)
  9. customThere were recovered 5.5 g (21%) of 5-nitro-2-trichloroacetylpyrrole in the form of a dark green oil and 11.2 g of 4-nitro-2-trichloroacetylpyrrole of melting point 160°-163° C.

Sources & evidence

ORD record
ord-7cbf9ec58dff48aaad87093d6b096f4a
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Reaction notes

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