Nitric Acid → HCID 21920981, compound

HRID 349585Notes

Reaction equation

HRID 349585 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].S(=O)(=O)(O)O>C(OCC)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH:9]2[CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[C:13]([N+:20]([O-:22])=[O:21])[CH:12]=3)[CH2:17]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10131276Ave-9488

Product 1

HCID 21920981HCID 21920981, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5.0 g (19.6 mmol) 4-fluoro-N-(indan-2-yl)-benzamide was given, at 5–10° C., a nitrating mixture of 10 ml conc. nitric acid and 12 ml conc. sulfuric acid, followed by stirring over 3 h at room temperature. The mixture was worked up by pouring onto an ice/water mixture, extraction with ethyl acetate, washing of the organic phase with a solution of sodium hydrogen carbonate, drying and evaporating to dryness. The thus-obtained residue was crystallized form ethyl acetate/heptane. yield: 3.2 g (54%), mp.: 167° C.

Workup

  1. customwas given, at 5–10° C.
  2. washwashing of the organic phase with a solution of sodium hydrogen carbonate
  3. customdrying
  4. customevaporating to dryness
  5. customThe thus-obtained residue was crystallized form ethyl acetate/heptane

Sources & evidence

ORD record
ord-0bf68223aa0d4ff39dc46f4603f206fc
Source dataset
uspto-grants-2007_02
Patent number
US07179839B2

Reaction notes

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