Formamide → 6-Iodoquinazolin-4-one

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=1[C:4](OC)=[O:5].[CH:13]([NH2:15])=O>>[I:12][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][CH:10]=1)[N:1]=[CH:13][NH:15][C:4]2=[O:5]

Participants

Reactant 2

HCID 713Formamide

HCID 847811Methyl 2-amino-5-iodobenzoate

Product 1

HCID 1354016666-Iodoquinazolin-4-one

Procedure

Methyl 2-amino-5-iodobenzoate (17.8 g, 64 mmol) was heated in 300 mL of formamide at 190° C. for 2 hours. The mixture was cooled to room temperature and the solid product was filtrated and dried in vacuum. The formed product 1403-174 was used without further purification. (10 g, 56.1%): LC-MS: 273 [M+1]+, 1H NMR (DMSO-d6): δ 7.46 (d, J=9.0 Hz, 1H), 8.10 (m, 2H), 8.36 (d, J=2.1 Hz, 1 H), 12.40 (s, 1H).

Workup

filtrationthe solid product was filtrated
customdried in vacuum
customThe formed product 1403-174 was used without further purification

Sources & evidence

ORD record: ord-5f5081b96f944a9a8f0992906fba70d9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024024B2

Reaction notes

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