N-Methyl-4-nitroaniline → 4-Quinazolinamine, N,2-dimethyl-N-(4-nitrophenyl)-

HRID 1876123Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-chloro-2-methylquinazoline (1.4 g, 7.84 mmol) and (4-nitro-phenyl)-methylamine (1.09 g, 7.16 mmol) in 20 mL of dimethylformamide cooled to 0° C. was added sodium hydride (0.6 g, 60 oil suspension, 15 mmol). The reaction mixture was stirred at 0° C. for 1 h and quenched by adding 200 uL of water. It was diluted with 150 mL of ethyl acetate, washed with water (100 mL×3), saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by chromatography (30% ethyl acetate/hexanes) to give the title compound (1.41 g, 4.78 mmol, 67%). 1H NMR (CDCl3): 8.14 (m, 2H), 7.91 (m, 1H), 7.71 (ddd, J=8.4, 6.6, 1.8, 1H), 7.19-7.32 (m, 2H), 7.05 (m, 2H), 3.76 (s, 3H), 2.82 (s, 3H).

Workup

customquenched
additionby adding 200 uL of water
additionIt was diluted with 150 mL of ethyl acetate
washwashed with water (100 mL×3), saturated NaCl
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography (30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-c132d5e55b9b40c4845650b849e546ee
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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