Benzoic acid, 3-amino-, methyl ester → HCID 54724161, compound

HRID 1866949Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[O:16][C:15](=O)[CH:14]=1>ClC1C=CC=CC=1Cl>[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[N:1]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[C:15](=[O:16])[CH:14]=1

Participants

Conditions

Temperature: 165 °C

Procedure

Methyl 3-aminobenzoate (75.00 g, 496.13 mmol) and 4-hydroxy-6-methyl-2-pyrone (62.57 g, 496.13 mmol) were suspended in 1,2-dichlorobenzene (150 mL) and heated to 165° C. for 15 minutes. The reaction was cooled to room temperature and extracted with 0.54M K2CO3 (4×250 mL). The aqueous layers were acidified (pH 2) with 4N HCl. The precipitate was collected by filtration to afford a yellow-orange solid (20.24 g, 16%). The resulting filtrate was extracted with ethyl acetate (3×1 L). The organic layers were washed with brine (500 mL), dried over MgSO4 and evaporated. The resulting solid was washed with hot H2O to afford a yellow-orange solid (3.84 g, 3%). The two solids were then combined. 1H NMR (400 MHz, DMSO-d6) δ 7.98 (dt, J=1.31, 7.79 Hz, 1H), 7.69 (app t, J=1.78 Hz, 1H), 7.62 (t, J=7.78 Hz, 1H) 7.49 (ddd, J=1.07, 1.07, 7.85 Hz, 1H), 5.89 (dd, J=087, 2.48 Hz, 1H), 5.55 (app d, J=0.94 Hz, 1H), 3.83 (s, 3H), 1.80 (s, 3H). ES-HRMS m/z 260.0895 (M+H C14H13NO4 requires 260.0917).

Workup

temperatureThe reaction was cooled to room temperature
extractionextracted with 0.54M K2CO3 (4×250 mL)
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-3b04ac4210d741cd95ff5061cf5760a0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629363B2

Reaction notes

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