Methanimidamide, hydrochloride (1:1) → 7-ethoxy-6-methoxyquinazolin-4(3H)-one

HRID 631189Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]([O:15][CH3:16])=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[CH:18](N)=[NH:19]>C(N)=O>[CH2:13]([O:12][C:10]1[CH:11]=[C:2]2[C:3]([C:4](=[O:5])[NH:19][CH:18]=[N:1]2)=[CH:8][C:9]=1[O:15][CH3:16])[CH3:14]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 2-amino-4-ethoxy-5-methoxybenzoate (4.43 g, 19.7 mmol) and formamidine hydrochloride (2.255 g, 28 mmol) in formamide (20 mL) was heated at 130° C. for 8 hours. The reaction mixture was quenched with water, filtered, washed with water, and dried under vacuum with P2O5 to give 7-ethoxy-6-methoxyquinazolin-4(3H)-one as solid (3.029 g, 70%). 1H NMR (300 MHz, DMSO-d6) δ 12.1 (br, 1H), 7.97 (s, 1H), 7.43 (s, 1H), 7.10 (s, 1H), 4.16 (q, 2H), 3.87 (s, 3H), 1.38 (t, 3H); LC-MS (ESI) m/z 221 (M+H)+.

Workup

customThe reaction mixture was quenched with water
filtrationfiltered
washwashed with water
dry with materialdried under vacuum with P2O5

Sources & evidence

ORD record: ord-b46c90c747af49aa85056338049111ee
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09320739B2

Reaction notes

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