Triethylamine → (2-Amino-4-methoxyphenyl)amide

HRID 2243349Notes

Reaction equation

HRID 2243349 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[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:2]([O:34][CH:21]([CH3:20])[CH3:22])([CH3:7])[CH3:3].[NH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[NH-:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1534044-Methoxy-o-phenylenediamineHCID 87540947Fluoren-4-one-9-carboxylic acid chloride

Product 2

HCID 7914Diisopropyl EtherHCID 86621037(2-Amino-4-methoxyphenyl)amideYield 124.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 10 g of 1,2-diamino-4-methoxybenzene, 20 ml of triethylamine and 17 g of fluoren-4-one-9-carboxylic acid chloride in 600 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 6.2 g of (2-amino-4-methoxyphenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid, in the form of a brown 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-799ce49072ff449aa2a9213014e0f8e3
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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