2-Hydroxyisobutyric acid → HCID 63015961, compound

HRID 1486783Notes

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].[OH:13][C:14]([CH3:19])([CH3:18])[C:15](O)=O.[OH-].[Na+]>Cl>[OH:13][C:14]([C:19]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)([CH3:18])[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2,3-diaminobenzoic acid methyl ester (1.5 g, 9.2 mmol) in 4 M HCl (50 mL) was added 2-hydroxyisobutyric acid (2.87 g, 27.6 mmol). The mixture was stirred at ˜90° C. for 24 h. It was neutralized by use of aqueous sodium hydroxide solution to pH-3, and concentrated to dryness. The residue was suspended in methanol, and filtered through a filter paper. The filtrate was concentrated and the residue was rinsed with ether. The remaining solid residue was dissolved in ethyl acetate, and washed with brine solution. After drying over MgSO4, the organic solution was evaporated in vacuo, yielding the title intermediate as a pale yellow oil (˜800 mg). The crude product was used in the next step without further purification. (m/z): [M+H]+ calcd for C11H12N2O3 221.09. found 221.1. 1H-NMR (CD3OD) δ (ppm) 7.8 (dd, 1H), 7.7 (dd, 1H), 7.2 (m, 1H), 1.3 (s, 6H).

Workup

concentrationconcentrated to dryness
filtrationfiltered through a filter paper
concentrationThe filtrate was concentrated
washthe residue was rinsed with ether
dissolutionThe remaining solid residue was dissolved in ethyl acetate
washwashed with brine solution
dry with materialAfter drying over MgSO4
customthe organic solution was evaporated in vacuo

Sources & evidence

ORD record: ord-c4ec4950cc994159bbdefb9b2f3c288c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428489B2

Reaction notes

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