N,N-Dimethylaniline → HCID 18535765, compound

HRID 365384Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[N:6]=[CH:5][N:4]=1.[CH2:16]([O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)C1C=CC=CC=1>C(O)(C)C>[ClH:2].[NH2:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[CH:5][N:4]=[C:3]2[NH:28][C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of crude 4-chloro-6-nitroquinazoline hydrochloride (5 mmol) (Morley J. S. and Simpson J. C. E., J. Chem. Soc., 1948:360) was refluxed under nitrogen with stirring in isopropanol (10 mL) containing 4-benzyloxyaniline (999 mg, 5 mmol) and N,N-dimethylaniline (1.209 g, 10 mmol) for 3 hours. The mixture was allowed to cool to 25° C., and the precipitate was collected by Buchner filtration, rinsed with isopropanol (2×10 mL), and dried at 60° C. in a vacuum oven to give 6-amino-4-(4-benzyloxyanilino)quinazoline hydrochloride (1.675 g, 82%) as a mustard yellow solid; mp 246°248° C. Calculated for C21H16N4O3.HCl: C, 61.69; H, 4.19; N, 13.71%. Found: C, 61.72; H, 4.22; N; 13.52%. 1H NMR (DMSO-d6): δ11.98 (1 H, brs), 9.85 (1 H, d, J=2.2 Hz), 8.94 (1 H, s), 8.76 (1 H, dd, J=2.3, 9.1 Hz), 8.15 (1 H, d, J=9.3 Hz), 7.65 (2 H, d, J=9.0 Hz), 7.48 (2 H, d, J=7.0 Hz), 7.41 (2 H, t, J=7.4 Hz), 7.31 (1 H, t, J=7.4 Hz), 7.15 (2 H, d, J=9.1 Hz), 5.16 (2 H, s). Mass spectrum (APCI) 373 (100 MH+).

Workup

temperaturewas refluxed under nitrogen
filtrationthe precipitate was collected by Buchner filtration
washrinsed with isopropanol (2×10 mL)
customdried at 60° C. in a vacuum oven

Sources & evidence

ORD record: ord-e7be5808b8c5488eba8f690f7d7f6f6c
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127374

Reaction notes

Loading…