Ammonia → 8-Nitro-4-oxo-4H-1-benzopyran-2-carboxamide

HRID 1603881Notes

Reaction equation

HRID 1603881 reaction equation
[NH3:1].[N+:2]([C:5]1[C:14]2[O:13][C:12]([C:15](OCC)=[O:16])=[CH:11][C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([O-:4])=[O:3]>C(O)C.O1CCCC1>[N+:2]([C:5]1[C:14]2[O:13][C:12]([C:15]([NH2:1])=[O:16])=[CH:11][C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 100840998-nitro-2-ethoxycarbonyl-4-oxo-4H-1-benzopyran

Product 1

HCID 196062688-Nitro-4-oxo-4H-1-benzopyran-2-carboxamideYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Gas ammonia was bubbled for 30 minutes in a solution of ethyl 8-nitro-4-oxo-4H-benzopyran-2-carboxylate (2.109 g, 8.02 mmol) in anhydrous ethanol (50 ml) and anhydrous tetrahydrofuran (50 ml). After that the mixture was evaporated to dryness and the resulting solid residue was suspended in concentrated hydrochloric acid (20 ml) stirring at room temperature for 4 h. Then the mixture was diluted with water, the solid was recovered by filtration, washed repeatedly with water and dried under vacuum on phosphorous pentoxyde, to obtain 1.515 g of the title product (81% yield).

Workup

  1. customAfter that the mixture was evaporated to dryness
  2. additionThen the mixture was diluted with water
  3. filtrationthe solid was recovered by filtration
  4. washwashed repeatedly with water
  5. customdried under vacuum on phosphorous pentoxyde

Sources & evidence

ORD record
ord-46708ea962d740968b8542aea6ba0d32
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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