5-(3-Dimethylaminopropoxy)-4-fluoro-2-nitrophenylamine → 4-(3-Dimethylaminopropoxy)-5-fluorobenzene-1,2-diamine

HRID 2274390Notes

Reaction equation

HRID 2274390 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([F:17])=[CH:9][C:10]([N+:14]([O-])=O)=[C:11]([NH2:13])[CH:12]=1.[H][H]>CO.[Pd]>[CH3:18][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([NH2:13])[C:10]([NH2:14])=[CH:9][C:8]=1[F:17]

Participants

5

Reactant 2

HCID 578128495-(3-Dimethylaminopropoxy)-4-fluoro-2-nitrophenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 578128554-(3-Dimethylaminopropoxy)-5-fluorobenzene-1,2-diamineYield 104.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.8 g of 5-(3-dimethylaminopropoxy)-4-fluoro-2-nitrophenylamine in solution in 100 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 400 mg of palladium-on-charcoal at 25° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 3.5 g of 4-(3-dimethylaminopropoxy)-5-fluorobenzene-1,2-diamine are isolated in the form of a black oil. 1H NMR (400 MHz, DMSO-d6, δ in ppm): 1.75 (m, 2H); 2.13 (m, 6H); 2.32 (m, 2H); 3.84 (m, 2H); 4.3 (m, 4H); 6.32 (m, 2H).

Workup

  1. customThe reaction crude
  2. filtrationis filtered through celite
  3. concentrationthe filtrate is concentrated under vacuum in a rotary evaporator

Sources & evidence

ORD record
ord-27f1122fbe0343e8b57004497859464d
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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