Isobutyric Acid → HCID 58932987, compound

HRID 1437800Notes

Reaction equation

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

Participants

Conditions

Temperature: 10 °C

Procedure

A slurry of 2,3-diaminobenzoic acid methyl ester (21.5 g, 0.13 mol) and isobutyric acid (36.2 mL, 0.39 mol) in aqueous hydrochloric acid (4M, 210 mL) was stirred under reflux for 24 h to afford a homogenous solution. The solution was cooled to 10° C. and the pH raised to 3.5 using aqueous sodium hydroxide solution (4M, approx. 210 mL), while maintaining the temperature below 30° C. The reaction mixture was stirred at room temperature for 2 h, cooled to 10° C., and the resultant precipitate filtered off. The solid cake was transferred to a beaker and acetonitrile (300 mL) was added. The slurry was stirred at room temperature for 1 h then and filtered to afford a grey solid. The solid was dried under vacuum to afford the title intermediate (23 g, 0.1 1 mol, 87%). (m/z): [M+H]+ calcd for C11H12N2O2 calcd. 205.09; found 205.3. 1H NMR (300 MHz, DMSO-d6): δ (ppm) 1.27 (d, 6H), 3.39 (m, 1H), 7.29 (t, 1H), 7.78 (m, 2H).

Workup

temperatureunder reflux for 24 h
customto afford a homogenous solution
temperaturewhile maintaining the temperature below 30° C
temperaturecooled to 10° C.
filtrationthe resultant precipitate filtered off
additionwas added
stirringThe slurry was stirred at room temperature for 1 h
filtrationfiltered
customto afford a grey solid
customThe solid was dried under vacuum

Sources & evidence

ORD record: ord-42c9ce7beff2405296262ba1078f6381
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622587B2

Reaction notes

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