m-Toluidine → HCID 19963135, compound

HRID 2210022Notes

Reaction equation

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

Participants

Reactant 2

HCID 7934m-Toluidine

HCID 21717193153437-50-4

Product 1

HCID 19963135HCID 19963135, compoundYield 76%

Procedure

Using an analogous procedure to that described in Example 1, 4-chloro-6-morpholinoquinazoline was reacted with 3-methylaniline to give 4-(3'-methylanilino)-6-morpholinoquinazoline hydrochloride in 76% yield, m.p. 276°-278° C. NMR Spectrum: (CD3SOCD3) 2.38 (s, 3H), 3.41 (m, 4H), 3.82 (m, 4H), 7.18 (d, 1H), 7.38 (m, 1H), 7.48 (s, 1H), 7.50 (d, 1H), 7.87 (s, 2H), 8.08 (s, 1H), 8.75 (s, 1H); Elemental Analysis: Found C, 63.9; H, 6.0; N, 15.4; C19H20N4O 1HCl requires C, 64.1; H, 5.9; N, 15.8%.

Sources & evidence

ORD record: ord-63ee18b119584287a43469b09ead08de
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457105

Reaction notes

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