3-Aminophenol → 3-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline

HRID 871438Notes

Reaction equation

HRID 871438 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1>>[CH3:21][O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:22][CH2:23][CH2:24][O:25][CH3:26])[N:13]=[CH:12][N:11]=[C:10]2[O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

3

Reactant 2

HCID 115683-AminophenolHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

Product 1

HCID 668758053-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)anilineYield 34%

Procedure

Using the procedure described in Example 46, 3-aminophenol (1.21 g, 11.1 mmol) and 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (2.85 g, 10.6 mmol) were reacted to give 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline (1.22 g, 3.58 mmol, 34%). 1H NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1H), 7.52 (s, 1H), 7.39 (s, 1H), 7.09 (t, 1H), 6.50 (d, 1H), 6.53 (s, 1H), 6.40 (d, 1H), 5.30 (br s, 2H), 4.33 (t, 2H), 3.97 (s, 3H), 3.77 (t, 2H), 3.31 (s, 3H); LC-MS (ESI) m/z 342 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c0b2140551894277a1aac4ce473114d2
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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