2-(4-Aminophenyl)ethylamine → HCID 67219024, compound

HRID 1468986Notes

Reaction equation

HRID 1468986 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>C(O)CCC>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][NH:16][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 728952-(4-Aminophenyl)ethylamineHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 67219024HCID 67219024, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-chloro-6,7-dimethoxy-quinazoline (2 g, 8.92 mmol) and 4-(2-amino-ethyl)-phenyl amine (1.3 g, 9.82 mmol) in 1-butanol (20 mL) was heated at 80° C. overnight. After the solution was cooled to room temperature, the solvent was removed and the residue was purified by silica gel column chromatography (eluted by 5% methanol in CH2Cl2) to get the title compound (2.3 g, 68%). 1H-NMR (300 MHz CDCl3) δ 8.57 (s, 1H), 7.19 (s, 1H), 7.48 (d, 2H, J=8.1 Hz), 6.66 (d, 3H, J=7.8 Hz), 5.36 (t, 1H, NH), 4.00 (s, 3H), 3.93 (s, 1H), 3.85 (q, 2H, J=6.6 Hz), 3.62 (s, 1H), 2.92 (t, 2H, J=6.6 Hz).

Workup

  1. customthe solvent was removed
  2. customthe residue was purified by silica gel column chromatography (eluted by 5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-f61f4f9c8e2848108ada56da67142a5e
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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