372510-71-9 → 3-Butylbenzenamine

HRID 326608

Reaction equation

HRID 326608 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([N+:11]([O-])=O)[CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH:3][CH3:4].[H][H]>[Pd]>[CH2:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 53672195372510-71-9HCID 178418361HCID 178418361, compound

Product 1

HCID 793333-ButylbenzenamineYield 89.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of 3-nitrobenzaldehyde (8.2 g) with propyltriphenyl phosphonium bromide (25 g) and n-butyllithium in hexane (64.9 mmol), as described in Example 1a, gave 3-(2-butenyl)nitrobenzene (9.3 g), δ (360 MHz, CDCl3) 1.1 (3H, t, CH3), 2.4 (2H, m, CH2CH3). 5.8 (1H, m, =CH--CH2), 6.3 (1H, m, CH=CH2), 7.2 to 8.0 (4H, m, ArH). Treatment of the above 3-(2-butenyl)nitrobenzene (9.3 g) with hydrogen and palladium on carbon (10%, 0.93 g) as described in Example 1a, gave 3-butylaniline (7.0 g), δ (60 MHz, CDCl2) 0.9 (3H, t, CH3), 1.4 (4H, m, CH2CH2CH3), 2.5 (2H, t, ARCH2), 3.4 (2H, bs, NH2 ) and 6.2 to 7.0 (4H, m, ArH).

Sources & evidence

ORD record
ord-343c67ab73dc4425bd20edd2799319af
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Linked notes

Loading…