Aniline → HCID 131714937, compound

HRID 2290519Notes

Reaction equation

HRID 2290519 reaction equation
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6]C(OCC)=O)=[O:5].C(O[CH:22]([O:26]CC)[O:23][CH2:24][CH3:25])C.[C:29](OC(=O)C)(=[O:31])[CH3:30].N[C:37]1C=CC=C[CH:38]=1>C(O)(C)C>[F:18][C:13]1[CH:12]([CH:30]([CH:29]=[O:31])[C:22]([O:23][CH2:24][CH3:25])=[O:26])[C:3](=[C:4]([O:5][CH2:37][CH3:38])[CH3:6])[C:2]([F:1])=[C:15]([F:16])[C:14]=1[F:17]

Participants

6

Reactant 4

HCID 6115AnilineHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

Product 1

HCID 131714937HCID 131714937, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 3.0 g (11.33 mmol) of 2-(2,3,4,5-tetrafluorobenzoyl)acetic acid, ethyl ester was added 2.49 g of triethylorthoformate and 2.76 g of acetic anhydride. The mixture was refluxed for two hours and was concentrated under high vacuum at 80° C. to dryness. The residual oil was treated with 1.05 g (1.0 equivalent) of aniline dissolved in 70 ml of isopropyl alcohol. After 24 hours the mixture was concentrated and the solid triturated with hexane. Filtration gave 2.88 g of 2,3,4,5,-tetrafluoro-β-oxo-α-1-ethoxyethylidene-phenylpropanoic acid, ethyl ester, mp 101°-103° C.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. concentrationwas concentrated under high vacuum at 80° C. to dryness
  3. concentrationAfter 24 hours the mixture was concentrated
  4. customthe solid triturated with hexane
  5. filtrationFiltration

Sources & evidence

ORD record
ord-c64ca49d22a84d3cb84131e66b637891
Source dataset
uspto-grants-1986_10
Patent number
US04617308

Reaction notes

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