1-Naphthylamine → HCID 58707282, compound

HRID 1910583Notes

Reaction equation

HRID 1910583 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[S:22]([CH3:25])(=[O:24])=[O:23]>CN(C)C=O.O>[F:21][C:19]1[CH:20]=[CH:15][C:16]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:17]([NH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 86401-NaphthylamineHCID 24758Sodium hydrideHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzene

Product 1

HCID 58707282HCID 58707282, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Naphthalen-1-amine (0.89 g, 4.7 mmol) and 60% NaH in oil (0.24 g, 6.1 mmol) were stirred in N,N-dimethylformamide (5 mL) for 15 min at 0° C. and for 30 min at room temperature. 2,4-Difluoro-1-(methylsulfonyl)benzene (0.67 g, 4.7 mmol), was added to the reaction as a solid. The reaction was allowed to stir at room temperature for 16 h. The reaction was poured in water and extracted with ether. After removal of solvent the crude was purified on silica chromatography in 10% ethyl acetate in hexanes to obtain 0.56 g of product (0.36 mg, 38% yield). 1H NMR (400 MHz, CDCl3): δ 8.30 (s, 1H), 7.89 (m, 3H), 7.54 (m, 5H), 6.79 (t, 1H), 6.48 (d, 1H), 3.22 (s, 3H).

Workup

  1. extractionextracted with ether
  2. customAfter removal of solvent the crude
  3. customwas purified on silica chromatography in 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5fa01f600e564c83be6de2ff5e2cc0cf
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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