3-Iodoaniline → N-(3-Iodophenyl)-6-nitroquinazolin-4-amine

HRID 346419Notes

Reaction equation

HRID 346419 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1>C(O)(C)C>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 122713-IodoanilineHCID 113562574-Chloro-6-nitroquinazoline

Product 1

HCID 21080003N-(3-Iodophenyl)-6-nitroquinazolin-4-amineYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Iodoaniline (12.57 grams, 57 mmol) was reacted with 4-chloro-6-nitroquinazoline (4 grams, 57 mmol), in iso-propylalcohol, as is described hereinabove, to give 4-[(3-iodophenyl)amino]-6-nitroquinazoline (5.99 grams, 78% yield), which was thereafter reacted (620 mg, 1.58 mmol) with hydrazine hydrate and Raney®Nickel, according to the procedure described hereinabove, to give 4-[(3-iodophenyl)amino]-6-aminoquinazoline (180 mg, 31% yield).

Sources & evidence

ORD record
ord-b6f4ab0b85ea476d80439c94a6fea092
Source dataset
uspto-grants-2007_02
Patent number
US07172749B2

Reaction notes

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