Aluminium lithium hydride → N-(2-aminobenzyl)-3-fluoro-4-methoxyaniline

HRID 2241225Notes

Reaction equation

HRID 2241225 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([F:21])[CH:14]=1)=O>O1CCOCC1>[NH2:7][C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=1[CH2:10][NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([F:21])[CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 433804092-amino-N-(3-fluoro-4-methoxyphenyl)benzamide

Product 1

HCID 66385653N-(2-aminobenzyl)-3-fluoro-4-methoxyaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred suspension of lithium aluminum hydride (121 mg, 3.2 mmol) in 2 mL dioxane at reflux under nitrogen was added 2-amino-N-(3-fluoro-4-methoxyphenyl)benzamide (260 mg, 1 mmol) as a solution in 2 mL dioxane. After refluxing overnight the reaction was cooled to room temperature and quenched by sequential treatment with H2O (150 μL), 15% NaOH (150 μL) and H2O (450 μL). After stirring for several minutes, the heterogeneous mixture was filtered through GF/F filter paper with dioxane and concentrated to a brown residue (246 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 7.14 (m, 2H), 6.86 (m, 1H), 6.74 (m, 2H), 6.60 (dd, 1H), 6.42 (dd, 1H), 4.15 (d, 2H), 4.12 (br s, 2H), 3.83 (s, 3H), 3.54 (br s, 1H).

Workup

  1. temperatureat reflux under nitrogen
  2. temperatureAfter refluxing overnight the reaction
  3. customquenched by sequential treatment with H2O (150 μL), 15% NaOH (150 μL) and H2O (450 μL)
  4. filtrationthe heterogeneous mixture was filtered through GF/F
  5. filtrationfilter paper with dioxane
  6. concentrationconcentrated to a brown residue (246 mg, 100%)

Sources & evidence

ORD record
ord-2075e00cba044b8abd8bc455057b3136
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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