Water → 3-(4-Methylphenyl)propan-1-amine

HRID 280326Notes

Reaction equation

HRID 280326 reaction equation
C[C:2]1C=C[C:5]([CH:8](C)[C:9]([NH2:11])=O)=[CH:4][CH:3]=1.[Li].O.[OH-].[Na+].O1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH3:18][C:19]1[CH:2]=[CH:3][C:4]([CH2:5][CH2:8][CH2:9][NH2:11])=[CH:21][CH:20]=1

Participants

6

Reactant 5

HCID 962Water2×HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 3028194LithiumHCID 156283352-(4-Methylphenyl)propionamide

Product 1

HCID 125642703-(4-Methylphenyl)propan-1-amine

Procedure

2-(4-Methylphenyl)propionamide (4 g) in dry tetrahydrofuran was added dropwise under nitrogen to lithium alumimium hydride (0.93 g) in dry tetrahydrofuran. The mixture was refluxed for 1 h at the end of addition. Water (1 ml), 2N. NaOH (1 ml), further water (3 ml) were added, the mixture filtered and the filtrate evaporated to give 3-(4-methylphenyl)propanamine (3.5 g).

Workup

  1. temperatureThe mixture was refluxed for 1 h at the end of addition
  2. filtrationthe mixture filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-df22234db89d499b8b5fcdf34a6d839c
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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