Hydrochloric Acid → 2-(3,4,5-Trimethoxyphenyl)quinazoline-4-carboxylic acid

HRID 717354Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21]([C:23]([O:25]C)=[O:24])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH-].[Na+].Cl>CO>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[N:22]=[C:21]([C:23]([OH:25])=[O:24])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 75 °C

Procedure

Into a 250-mL 3-necked round-bottom flask, was placed methyl 2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylate (1.7 g, 4.80 mmol, 1.00 equiv), methanol (10 mL) and sodium hydroxide (20%, 10 mL). The resulting solution was stirred for 30 min at 75° C. The pH value of the solution was adjusted to 2 with hydrogen chloride (1 mol/L). The resulting solution was extracted with 2×50 mL of dichloromethane and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.8 g (49%) of 2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 3.99 (s, 3H), 4.06 (s, 6H), 7.77-7.81 (m, 1H), 7.84 (s, 2H), 8.03-8.07 (m, 1H), 8.22 (d, 1H), 9.41 (d, 1H); MS (ESI) m/z 341 ([M+H]+).

Workup

customInto a 250-mL 3-necked round-bottom flask, was placed
extractionThe resulting solution was extracted with 2×50 mL of dichloromethane
dry with materialThe mixture was dried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
customThis resulted in 0.8 g (49%) of 2-(3,4,5-trimethoxyphenyl)quinazoline-4-carboxylic acid as a yellow solid

Sources & evidence

ORD record: ord-0c5882e1f8424414937d8d2c212c312f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193707B2

Reaction notes

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