HCID 58071393, compound → HCID 58071401, compound

HRID 1797919Notes

Reaction equation

HRID 1797919 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-6e521f7d9154464dac5f6ce0fc1e0856
Source dataset
uspto-grants-2013_01
Patent number
US08343954B2

Reaction notes

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