Acetic Acid → 6-Iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid

HRID 641965Notes

Reaction equation

[NH2:1][C:2]1[C:10]([C:11]([OH:13])=O)=[CH:9][C:8]([I:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15](OC)(OC)OC.C(O)(=O)C.[NH2:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[CH3:37])[C:30]([O:32][CH3:33])=[O:31]>C1(C)C=CC=CC=1>[I:14][C:8]1[CH:9]=[C:10]2[C:2](=[C:3]([C:4]([OH:6])=[O:5])[CH:7]=1)[N:1]=[CH:15][N:26]([C:27]1[CH:28]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:34]=[CH:35][C:36]=1[CH3:37])[C:11]2=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension 2-amino-5-iodoisophthalic acid (30.4 g) and in toluene (300 ml) was added trimethyl orthoformate (60 ml) followed by acetic acid (5.6 ml). The reaction mixture was stirred at 100° C. for 4 hours when additional trimethyl orthoformate (30 ml) and acetic acid (5.6 ml) was added and the heating continued for a further 21 hours. Methyl 3-amino-4-methylbenzoate (10.9 g) was added and the reaction mixture stirred at 100° C. for 21 hours. The reaction mixture was cooled to room temperature and the resultant solid collected by filtration, washed MeOH and dried in vacuo for 18 hours to yield 6-iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid as a white solid (21.1 g); NMR Spectrum: (DMSOd6) 2.20 (s, 3H), 3.85 (s, 3H), 7.61 (d, 1H), 8.02 (m, 1H), 8.08 (s, 1H), 8.54 (m, 1H), 8.62 (m, 2H); Mass Spectrum: M+H+ 465.

Workup

additionwas added
temperatureThe reaction mixture was cooled to room temperature
filtrationthe resultant solid collected by filtration
washwashed MeOH
customdried in vacuo for 18 hours

Sources & evidence

ORD record: ord-04a50319fa4c490abc0e8598e7b88059
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696215B2

Reaction notes

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