2-Iodoaniline → HCID 11056893, compound

HRID 1403079Notes

Reaction equation

HRID 1403079 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[F:9][C:10]([F:20])([F:19])[C:11](=O)[CH2:12][C:13](OCC)=[O:14].[OH-].[Na+]>>[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[NH:4][C:11]([C:10]([F:20])([F:19])[F:9])=[CH:12][C:13]2=[O:14]

Participants

4

Reactant 3

HCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 11056893HCID 11056893, compoundYield 42.3%

Conditions

Temperature
180 °C

Procedure

A mixture of 2-iodoaniline (25.0 g), ethyl 4,4,4-trifluoro-3-oxobutanoate (20.8 g), and PPA (78.0 g) was stirred at 180° C. for 1 hour. After cooling, the reaction solution was neutralized with an aqueous sodium hydroxide solution, and the deposit was filtered and washed with water. The filtrate was rendered acidic with hydrochloric acid, and the deposit was filtered and washed with water. The filtration residues were dried under reduced pressure to obtain compound (3a) (16.2 g, 42%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe deposit was filtered
  3. washwashed with water
  4. filtrationthe deposit was filtered
  5. washwashed with water
  6. customThe filtration residues were dried under reduced pressure

Sources & evidence

ORD record
ord-06a1a79169f3446a9424534ebbb66249
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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