Hydrochloric Acid → 4-((1,2-Dihydro-3-methyl-1-oxobenz[f]quinazolin-9-yl)methoxy)benzoic acid

HRID 381601Notes

Reaction equation

COC[N:4]1[C:13](=[O:14])[C:12]2[C:11]3[CH:15]=[C:16]([CH2:19][O:20][C:21]4[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=4)[CH:17]=[CH:18][C:10]=3[CH:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH3:32].Cl>C1COCC1.O>[CH3:32][C:5]1[NH:4][C:13](=[O:14])[C:12]2[C:11]3[CH:15]=[C:16]([CH2:19][O:20][C:21]4[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH:17]=[CH:18][C:10]=3[CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of ethyl 4-((1,2-dihydro-2-methoxymethyl-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methoxy)benzoate in THF:1N HCl: concentrated HCl (15:10:1, 26 ml) was stirred at 60° C. overnight. The resulting suspension was diluted with water, concentrated in vacuo to remove the THF, and chilled in an ice bath. The solid was filtered, washed with water, and dried in vacuo at 100° C. The resulting ester was dissolved in 1N NaOH (10 ml) and ethanol (˜3 ml) and stirred at 60° C. for 4 hours. The solution was acidified with concentrated HCl to pH 1.5 and the resulting precipitate filtered and dried in vacuo at 110° C. to give 4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methoxy)benzoic acid (0.195 g). 1H NMR (DMSO-d6, 300 MHz) δ: 2.59 (s, 3H, CH3), 5.46 (s, 2H, CH2O), 7.17 (d, J=9 Hz, 2H, Ar), 7.80 (overlapping d, J=9 Hz, 2H, Ar), 7.91 (d, J=9 Hz, 2H, Ar), 8.16 (d, J=8 Hz, 1H, Ar), 9.85 (s, 1H, Ar).

Workup

concentrationconcentrated in vacuo
customto remove the THF
temperaturechilled in an ice bath
filtrationThe solid was filtered
washwashed with water
customdried in vacuo at 100° C
dissolutionThe resulting ester was dissolved in 1N NaOH (10 ml)
filtrationthe resulting precipitate filtered
customdried in vacuo at 110° C.

Sources & evidence

ORD record: ord-1b664cb880ea41e38147559dc033cb7b
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306865B1

Reaction notes

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