Triethylamine → (2-Amino-5-chloro-4-fluorophenyl)amide

HRID 2243340Notes

Reaction equation

HRID 2243340 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH2:10].C(N(CC)CC)C.C1C=[CH:20][C:21](=[O:34])[C:22]2C=1C(C(Cl)=O)=C1C=2C=CC=C1>ClCCl>[CH:21]([O:34][CH:7]([CH3:6])[CH3:2])([CH3:22])[CH3:20].[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH-:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7357734-Chloro-5-fluoro-1,2-phenylenediamineHCID 87540947Fluoren-4-one-9-carboxylic acid chloride

Product 2

HCID 7914Diisopropyl EtherHCID 131727949(2-Amino-5-chloro-4-fluorophenyl)amideYield 301.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 1 g of 1,2-diamino-4-chloro-5-fluorobenzene, 1.75 ml of triethylamine and 1.5 g of fluoren-4-one-9-carboxylic acid chloride in 45 ml of dichloromethane. After stirring for 20 hours at room temperature, the precipitate that formed is filtered off, and washed with dichloromethane, with water, then with a 10% saturated aqueous solution of sodium hydrogen carbonate and, finally, with water. After formation of a paste with diisopropyl ether, in this way we obtain 1.5 g of (2-amino-5-chloro-4-fluorophenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid, in the form of a yellow powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. customthe precipitate that formed
  2. filtrationis filtered off
  3. washwashed with dichloromethane, with water

Sources & evidence

ORD record
ord-bd376865731c4017a6a231c262439b35
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

Loading…