1-Naphthaldehyde → HCID 136247054, compound

HRID 2167232Notes

Reaction equation

S([O-])(O)=O.[Na+].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:17])=[C:12]([CH:16]=1)[C:13]([NH2:15])=[O:14].[C:18]1([CH:28]=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1>CN(C)C(=O)C>[CH3:6][O:7][C:8]1[CH:16]=[C:12]2[C:11](=[CH:10][CH:9]=1)[N:17]=[C:28]([C:18]1[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=1)[NH:15][C:13]2=[O:14]

Participants

Conditions

Temperature: 150 °C

Procedure

Sodium hydrogen sulfite (0.8 g, 7.5 mmol) was added to a solution of 5-methoxy-2-aminobenzamide (9) (1.2 g, 7.3 mmol) and 1-naphthaldehyde (14) (1.1 g, 7.3 mmol) in N,N-dimethylacetamide (DMAC) (20 mL). The mixture was heated with stirring at 150° C. for 3 h and poured into ice water (200 mL). The precipitate was collected, washed with water, and dried in vacuo. After purification by column chromatography (silica gel; chloroform) and then recrystallization from EtOH, 6-methoxy-2-(naphthalen-1-yl)-4-quinazolinone (17) was obtained (1.5 g, 70%) as pale yellow needles. The method used to prepare 17 was used with the indicated substituted benzaldehyde and benzamide to afford 18-31. Compounds 17-31 were further analyzed by the method as described in “General materials and method”. The properties of Compounds 17-31 were respectively described as below.

Workup

temperatureThe mixture was heated
customThe precipitate was collected
washwashed with water
customdried in vacuo
customAfter purification by column chromatography (silica gel; chloroform)
customrecrystallization from EtOH

Sources & evidence

ORD record: ord-76821a2ddb2b4d5aa02928381d921e4b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045437B2

Reaction notes

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