Acetic Acid → HCID 15345697, compound

HRID 259784Notes

Reaction equation

[CH2:1]1[O:3][CH2:2]1.[NH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9].[C:15](O)(=[O:17])[CH3:16]>O>[OH:17][CH2:15][CH2:16][N:4]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])[CH2:2][CH2:1][OH:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethylene oxide (16 mL, 330 mmol) was added rapidly via a cold syringe to a solution of methyl 3-aminobenzoate (5.0g, 33 mmol), glacial acetic acid (40 mL), and water (40 mL) with stirring at 0 ° C. under nitrogen beneath a dry ice/acetone condenser. After 1 h, the cold bath was removed and the reaction stirred for 43 h at room temperature. Water was added, and the mixture neutralized by adding solid sodium bicarbonate portionwise. After a series of EtOAc/H2O extractions, the crude product was isolated by concentration under reduced pressure. Purification by chromatography on silica gel, eluting with 0% to 5% MeOH in EtOAc, and evaporation yielded an oil (6.9 g). IR(neat): cm-1 3340, 1718. 1H NMR(300 MHz, CDCl3): 7.38-6.87 (m, 4H), 3.90-3.85 (m, 7H), 3.65-3.59 (m, 4H), 3.27 (s, 2H). HR-MS: Calc'd. 240.1236, Found 240.1237.

Workup

customthe cold bath was removed
stirringthe reaction stirred for 43 h at room temperature
additionWater was added
additionby adding solid sodium bicarbonate portionwise
extractionAfter a series of EtOAc/H2O extractions
customthe crude product was isolated by concentration under reduced pressure
customPurification by chromatography on silica gel
washeluting with 0% to 5% MeOH in EtOAc, and evaporation

Sources & evidence

ORD record: ord-ad598712f45f4cd1af4f4d8b12e62b80
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523302

Reaction notes

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