3-Fluoroaniline → 11N-112

HRID 365238Notes

Reaction equation

HRID 365238 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.ClC1C2C(=CC(OC)=C(OC)C=2)N=CN=1.[F:38]C1C=C(C=CC=1)N>>[F:38][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:6]=[CH:7][CH:2]=1

Participants

4

Reactant 3

HCID 97423-FluoroanilineHCID 14750636,7-DIMETHOXY-4-(P-FLUOROANILINO)-QUINAZOLINEHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 147488311N-112Yield 98%

Procedure

Employing the same method used for compound 1, 4-chloro-6,7-dimethoxyquinazoline (113 mg, 0.5 mmol) and 3-fluoroaniline (48 μL, 0.5 mmol) afforded compound 2 as the hydrochloride salt in 98% yield (166 mg). 1H NMR [((CD3)2SO) δ11.59(s, 1H), 8.85(s, 1H), 8.43(s, 1H), 7.7(m, 1H), 7.6(m,1H), 7.5(m, 1H), 7.4(s, 1H), 7.1(s, 1H), 4.1(s, 3H), 3.96(s, 3H). MS, m/e: 300 (M+), 299 [(M-H)+ ]. Anal. Calcd. for C16H15FClN3O2 : C, 57.14; H, 4.46; N, 12.50. Found: C, 57.09; H, 4.53; N, 12.49.

Sources & evidence

ORD record
ord-e5901cfd4f334a00a178ed7c8ae0ff39
Source dataset
uspto-grants-2000_10
Patent number
US06126917

Reaction notes

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