HCID 53255561, compound → HCID 53255729, compound

HRID 1041749Notes

Reaction equation

HRID 1041749 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][O:11][CH3:12])[C:3]=1[N+:13]([O-])=O.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][O:11][CH3:12])[C:3]=1[NH2:13]

Participants

5

Reactant 2

HCID 53255561HCID 53255561, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53255729HCID 53255729, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-fluoro-3-(2-methoxy-ethoxy)-2-nitro-benzene (675 mg) and Pd/C (10%, 30 mg) in ethanol was shaken under 50 psi of hydrogen for 4 hours. The reaction mixture was filtered through celite and concentrated to afford 580 mg of 2-fluoro-6-(2-methoxy-ethoxy)-phenylamine: 1H NMR (300 MHz, CDCl3) δ 6.8-6.7 (m 3H), 4.2 (t, 2H), 3.9 (bs, 2H), 3.8 (t, 2H), 3.5 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d3d0c6109f1944d0b6a1749d82421b46
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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