P-Phenylenediamine → 4-(4'-Aminoanilino)-6,7-dimethoxyquinazoline hydrochloride

HRID 2210025

Reaction equation

[Cl:1][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.[C:16]1([NH2:23])[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1>>[ClH:1].[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([NH:23][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:17][CH:18]=1

Participants

Reactant 2

HCID 7814P-Phenylenediamine

HCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 199632054-(4'-Aminoanilino)-6,7-dimethoxyquinazoline hydrochlorideYield 85%

Procedure

Using an analgous procedure to that described in Example 74, 4-chloro-6,7-dimethoxyquinazoline was reacted with 1,4-phenylenediamine to give 4-(4'-aminoanilino)-6,7-dimethoxyquinazoline hydrochloride in 85% yield, m.p. 274°-276° C. NMR Spectrum: (CD3SOCD3) 3.95 (s, 3H), 3.98 (s, 3H), 6.75 (d, 2H), 7.35 (s, 1H), 7.38 (d, 2H), 8.25 (s, 1H), 8.67 (s, 1H), 11.05 (broad s, 1H); Elemental Analysis: Found C, 57.6; H, 5.0; N, 16.9; C16H16N4O2. 1HCl requires C, 57.7; H, 5.15; N, 16.8%.

Sources & evidence

ORD record: ord-9d5d185f4a274d27a178db993bde2448
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457105

Linked notes

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