Butylamine → HCID 11266189, compound

HRID 1840711Notes

Reaction equation

HRID 1840711 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[Cl:6][C:7]1[C:16]2[C:11]3=[C:12]([C:17](=[O:21])N[C:19](=[O:20])[C:10]3=[CH:9][CH:8]=1)[CH:13]=[CH:14][CH:15]=2>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:17](=[O:21])[C:12]2=[C:11]3[C:16](=[CH:15][CH:14]=[CH:13]2)[C:7]([Cl:6])=[CH:8][CH:9]=[C:10]3[C:19]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 36487504-chloronaphthalene-1,8-dicarboximide

Product 1

HCID 11266189HCID 11266189, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound has been reported previously. This preparation is similar to previously reports (see e.g. Daffy et al. Chem-Eur J 1998, 4, 1810-1815; de Silva et al., Chem Rev 1997, 97, 1515-1566). A portion of n-butylamine (5.00 mL, 50.6 mmol) was added to a suspension of 4-chloronaphthalene-1,8-dicarboximide (11.7 g, 50.5 mmol) in 160 mL of toluene. This mixture was brought to reflux for 17 hours to give a dark black-brown solution. Crystallization from hexanes/toluene at −10° C. gave 1ax as a pure brownish-yellow powder (11.1 g, 76%). 1H NMR: δ=8.65 (d, 1H, J=7.4 Hz), 8.58 (d, 1H, J=8.6 Hz), 8.49 (d, 1H, J=7.9 Hz), 7.85 (t, 1H, J=7.9 Hz), 7.81 (d, 1H, J=7.9 Hz), 4.18 (t, 2H, J=7.6 Hz), 1.72 (m, 2H), 1.45 (m, 2H), 0.98 (t, 2H, J=7.4 Hz). 13C{1H} NMR: δ=163.8, 163.5, 139.0, 132.0, 131.2, 130.6, 129.3, 129.1, 127.9, 127.5, 123.2, 121.7, 40.5, 30.3, 20.5, 14.0. ESI/MS m/z.

Workup

  1. temperatureto reflux for 17 hours
  2. customto give a dark black-brown solution
  3. customCrystallization from hexanes/toluene at −10° C.

Sources & evidence

ORD record
ord-c2af2c53538e462f84c6359152e8cefd
Source dataset
uspto-grants-2004_01
Patent number
US06682938B1

Reaction notes

Loading…