4-Fluoro-5-(morpholin-4-yl)-2-nitroaniline → 4-Fluoro-5-morpholin-4-ylbenzene-1,2-diamine

HRID 2274381Notes

Reaction equation

HRID 2274381 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][C:5]([NH2:14])=[C:4]([N+:15]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:15])[C:5]([NH2:14])=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 29593374-Fluoro-5-(morpholin-4-yl)-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 15103004-Fluoro-5-morpholin-4-ylbenzene-1,2-diamineYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

35 g of 4-fluoro-5-morpholin-4-yl-2-nitrophenylamine in solution in 618 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 3.4 g of palladium-on-charcoal at 22° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 30 g of 4-fluoro-5-morpholin-4-ylbenzene-1,2-diamine in the form of a brown solid are isolated. 1H NMR (400 MHz, (CD3)2SO, δ in ppm): 2.78 (m: 4H); 3.68 (m: 4H); 4.25 (broad s: 2H); 4.35 (broad s: 2H); 6.27 (d, J=8 Hz: 1H); 6.31 (d, J=14 Hz: 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-37fb1059ff074932bebf300d9818eae6
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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