Benzyl (5-n-butyl-2-pyridyl)carbamate → 5-Butylpyridin-2-amine

HRID 1701398Notes

Reaction equation

HRID 1701398 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11]C(=O)OCC2C=CC=CC=2)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[H][H]>[Pd].C(O)C>[NH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 53891397Benzyl (5-n-butyl-2-pyridyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 184286505-Butylpyridin-2-amineYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl (5-n-butyl-2-pyridyl)carbamate (6.5 g. 22.86 mmoles) and 10% palladium on carbon (2.7 g.) in ethanol (400 ml.) was shaken at room temperature for 2 hours in an atmosphere of hydrogen at an initial pressure of 3.52 kg./cm.2The mixture was filtered and the filtrate reduced to dryness to leave 2-amino-5-n-butylpyridine (3.42 g., 99.7%), m.p. 30°-33° (lit. m.p. 35°-36° in Helv. Chim. Acta, 39, 505 (1956).

Workup

  1. filtration/cm.2The mixture was filtered

Sources & evidence

ORD record
ord-fda28c2772bb4d8687a1a874009ba9de
Source dataset
uspto-grants-1980_03
Patent number
US04192944

Reaction notes

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