Acetic Acid → 4-amino-5-(2-methylprop-1-enyl)quinazolin-2(1H)-one

HRID 711757Notes

Reaction equation

[C:1]([C:3]1[C:8]([CH:9]=[C:10]([CH3:12])[CH3:11])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:13][C:14]([NH:16]C(=O)C1C=CC=CC=1)=[O:15])#[N:2].[OH-].[Na+].CC(O)=O>CCO>[NH2:2][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:9]=[C:10]([CH3:12])[CH3:11])[NH:13][C:14](=[O:15])[N:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of N-(2-cyano-3-(2-methylprop-1-enyl)phenyl carbamoyl)benzamide (Example 150a) (0.133 g, 0.416 mmol) in EtOH (3 mL) was treated with a solution of NaOH (2 M, 0.416 mL, 0.832 mmol) at room temperature. The obtained mixture was heated at 90° C. for 30 min, cooled to room temperature and neutralized with 10% AcOH. The precipitated product was collected by filtration to give 69.0 mg (77%) of 4-amino-5-(2-methylprop-1-enyl)quinazolin-2(1H)-one as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.60 (d, J=1.2 Hz, 3H), 1.93 (d, J=1.2 Hz, 3H), 6.58 (s, 1H), 6.67 (broad s, 1H), 6.73 (m, 1H), 7.05 (m, 1H), 7.48 (m, 1H), 7.93 (broad s, 1H), 10.72 (broad s, 1H). MS 216 (MH+).

Workup

filtrationThe precipitated product was collected by filtration

Sources & evidence

ORD record: ord-3d645360e61d478e83bca9810ba4d960
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

Loading…