HCID 58071393, compound → HCID 58071401, compound

HRID 2178175Notes

Reaction equation

HRID 2178175 reaction equation
C([NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([CH3:17])=[C:11]([F:18])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[F:18][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[CH3:17])[NH2:8]

Participants

5

Reactant 2

HCID 58071393HCID 58071393, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58071401HCID 58071401, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyl-3-fluoro-5-methoxy-4-methylaniline (223 mg, 0.91 mmol) in methanol (25 mL) prepared in a Parr shaker flask was added palladium hydroxide (20% on carbon). This was subjected to 45 psi of hydrogen gas overnight until the LCMS showed complete conversion. The catalyst was filtered and the solution concentrated in vacuo to yield 117 mg (83%) of 3-fluoro-5-methoxy-4-methylaniline as an oil. 1H NMR (300 MHz, CDCl3) δ 6.03 (d, J=12.0 Hz, 1H), 6.01 (s, 1H), 3.77 (s, 3H), 2.09 (s, 3H); LCMS (m/z): 156 (MH+). Compound I-120 was made using this aniline.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-56b297441e094b39b3689d3e362c998f
Source dataset
uspto-grants-2015_06
Patent number
US09067925B2

Reaction notes

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