O-Phenylenediamine → N-(2-amino-phenyl)-5-bromo-2-fluoro-benzamide

HRID 2047387Notes

Reaction equation

HRID 2047387 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:12]1([NH2:19])[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C=O)C>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:19][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:11]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27363155-Bromo-2-fluorobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 24693313N-(2-amino-phenyl)-5-bromo-2-fluoro-benzamideYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-fluoro-benzoic acid (4.96 g, 22.6 mmol), benzene-1,2-diamine (4.90 g, 45.3 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (5.21 g, 27.2 mmol), 1-hydroxybenzotriazole hydrate (1-HOBt) (3.67 g, 27.2 mmol) and dimethyl-pyridin-4-yl-amine (DMAP) (0.03 g, 0.2 mmol) were placed into a 100 mL round bottom flask. Dry DMF (60 mL) was added and the reaction was stirred at room temperature overnight. Solvent was removed under reduced pressure, then the crude diluted with DCM (15 mL) and 0.4 M Na2CO3 solution (15 mL) A white precipitate formed and it was filtered off and washed again with DCM (10 mL) and dried to afford 4.96 g of the title compound. Solutions were collected, the organic phase was separated from the aqueous one and concentrated under reduced pressure: other precipitate formed and it was filtered off, washed with DCM (3 mL) to afford other 0.68 g of desired compound. Total yield 81%.

Workup

  1. customSolvent was removed under reduced pressure
  2. additionthe crude diluted with DCM (15 mL) and 0.4 M Na2CO3 solution (15 mL) A white precipitate
  3. customformed
  4. filtrationit was filtered off
  5. washwashed again with DCM (10 mL)
  6. customdried

Sources & evidence

ORD record
ord-74c9009bcd7344189865a893ce70d4a4
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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