1,3-Benzenediamine, 5-chloro- → HCID 18925005, compound

HRID 1288869Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) and 5-amino-3-chloroaniline (253 mg, 1.78 mmol) were combined in isopropanol (3 mL) and heated to reflux for 16 hours under an atmosphere of dry nitrogen. After cooling to 20° C. the mixture was diluted with methanol (5 mL) and the resulting precipitate was filtered and dried, in vacuo, to afford 252 mg (77%) of (3-amino-5-chlorophenyl)-(6,7-dimethoxyquinazolin-4-yl)amine hydrochloride (mp. 298°-301° C.; LC-MS: 331 (MH+)). A portion of this product (175 mg, 0.476 mmol) was dissolved in 80% acetic acid/H2O (12 mL), cooled to 0° C., and a solution of NaNO2 (36 mg, 0.516 mmol) in H2O (300 μL) was added. The solution was stirred for 10 minutes at 0° C. and NaN3 (33 mg, 0.50 mmol) in H2O (300 μL) was added. The reaction mixture was allowed to warm to 20° C. and stirred 16 hours. The resulting precipitate was filtered and dissolved in 10% methanol in CHCl3 and the solution was washed with saturated aqueous NaHCO3, and brine, dried over Na2 SO4, filtered and concentrated in vacuo to yield 59 mg (35%) of the title product as a yellow solid; mp 205°-206° C.

Workup

temperatureheated
temperatureto reflux for 16 hours under an atmosphere of dry nitrogen
filtrationthe resulting precipitate was filtered
customdried, in vacuo

Sources & evidence

ORD record: ord-66b9e3add87442c48b999279c1cfa58f
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747498

Reaction notes

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