3-Aminophenol → 4-(3-Hydroxyanilino)-6,7-Dimethoxyquinazoline

HRID 2210023Notes

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][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1>>[OH:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[NH:16][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

Participants

Reactant 2

HCID 115683-Aminophenol

HCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 56874-(3-Hydroxyanilino)-6,7-DimethoxyquinazolineYield 92%

Procedure

Using an analogous procedure to that described in Example 68, 4-chloro-6,7-dimethoxyquinazoline was reacted with 3-aminophenol to give 4-(3'-hydroxyanilino)-6,7-dimethoxyquinazoline in 92% yield, m.p. 256°-257° C. NMR Spectrum: 3.98 (s, 3H), 4.02 (s, 3H), 6.75 (m, 1H), 7.12 (d, 1H), 7.14 (d, 1H), 7.25 (t, 1H), 7.42 (s, 1H), 8.37 (s, 1H), 8.80 (s, 1H), 9.5 (broad hump, 1H), 11.4 (broad s, 1H); Elemental Analysis: Found C, 57.1; H, 4.8; N, 12.1; C16H15N3O3. 1HCl. 0.25H2O requires C, 56.8; H, 4.9; N, 12.4%.

Sources & evidence

ORD record: ord-ed0c400ca4b64649a38494f116608de0
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457105

Reaction notes

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