Diethyl Ether → 4-(1H-imidazol-5-yl)-N-methylaniline

HRID 979192Notes

Reaction equation

HRID 979192 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][CH:13]=O)=[CH:8][CH:7]=2)[N:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>O1CCCC1>[CH3:13][NH:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 178521891HCID 178521891, compound

Product 1

HCID 1784821004-(1H-imidazol-5-yl)-N-methylaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of N-[4-(imidazol-4-yl)-phenyl]-formamide (8 g) in anhydrous tetrahydrofuran (80 ml) was slowly added dropwise to a suspension of LiAlH4 (6.5 g) in anhydrous tetrahydrofuran. The reaction mixture was refluxed for 4 hours and cooled. Wet diethylether was added, and then the solution was evaporated to dryness. The residue was dissolved in water and ethylacetate. After working up the organic layer, 4.6 g of N-methyl-N-[4-(imidazol-4-yl)-phenyl]-amine, M.p. 75°-76° C., were obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. temperaturecooled
  3. customthe solution was evaporated to dryness
  4. dissolutionThe residue was dissolved in water
  5. customwere obtained

Sources & evidence

ORD record
ord-6b684fa9031646028208df807f1ff6ba
Source dataset
uspto-grants-1987_05
Patent number
US04666932

Reaction notes

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