Aniline → HCID 178418328, compound

HRID 1596529Notes

Reaction equation

HRID 1596529 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O=[C:13]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])(=O)C.[Na+]>Cl.O>[C:6]1([NH:5][N:1]=[C:13]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 517045Sodium AcetateHCID 14763927HCID 14763927, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178418328HCID 178418328, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

Sodium nitrite (2.57 g) was added portionwise to aniline (3.22 g) in concentrated HCl (6.5 ml) and water 10 ml) at 0° C. over 15 minutes. The resulting solution was added dropwise to ethyl 2,3-dioxo-4,4,4-trifluorobutanoate (6.31 g) and sodium acetate (6 g) in water (30 ml) at 0° C. to precipitate the product as a red solid which was filtered and dried in vacuo (7.15 g, 72%). The crude hydrazone was used without further purification.

Workup

  1. customto precipitate the product as a red solid which
  2. filtrationwas filtered
  3. customdried in vacuo (7.15 g, 72%)
  4. customThe crude hydrazone was used without further purification

Sources & evidence

ORD record
ord-0716c625072c4e639daa26725714aadf
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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